CN116003475A - Organometallic compound, organic light-emitting device including the same, and electronic apparatus including the organic light-emitting device - Google Patents
Organometallic compound, organic light-emitting device including the same, and electronic apparatus including the organic light-emitting device Download PDFInfo
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- CN116003475A CN116003475A CN202211293559.9A CN202211293559A CN116003475A CN 116003475 A CN116003475 A CN 116003475A CN 202211293559 A CN202211293559 A CN 202211293559A CN 116003475 A CN116003475 A CN 116003475A
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- 150000002902 organometallic compounds Chemical class 0.000 title claims abstract description 66
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 44
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 40
- 125000006756 (C5-C30) carbocyclic group Chemical group 0.000 claims abstract description 26
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 17
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 13
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 13
- 239000003446 ligand Substances 0.000 claims abstract description 11
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 11
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 5
- 239000010410 layer Substances 0.000 claims description 145
- -1 cyano, nitro, amino, amidino, hydrazino Chemical group 0.000 claims description 84
- 150000003839 salts Chemical class 0.000 claims description 81
- 125000003118 aryl group Chemical group 0.000 claims description 79
- 125000000217 alkyl group Chemical group 0.000 claims description 55
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 53
- 150000001875 compounds Chemical class 0.000 claims description 45
- 238000002347 injection Methods 0.000 claims description 37
- 239000007924 injection Substances 0.000 claims description 37
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 36
- 229910052805 deuterium Inorganic materials 0.000 claims description 36
- 230000005525 hole transport Effects 0.000 claims description 35
- 125000001624 naphthyl group Chemical group 0.000 claims description 29
- 125000003367 polycyclic group Chemical group 0.000 claims description 28
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
- 239000012044 organic layer Substances 0.000 claims description 27
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 26
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims description 26
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 26
- 150000007857 hydrazones Chemical class 0.000 claims description 26
- 125000004585 polycyclic heterocycle group Chemical group 0.000 claims description 26
- 125000006753 (C1-C60) heteroaryl group Chemical group 0.000 claims description 25
- 125000004366 heterocycloalkenyl group Chemical group 0.000 claims description 25
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 24
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 24
- 125000006744 (C2-C60) alkenyl group Chemical group 0.000 claims description 23
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 23
- 125000006746 (C1-C60) alkoxy group Chemical group 0.000 claims description 22
- 125000006745 (C2-C60) alkynyl group Chemical group 0.000 claims description 22
- 125000006751 (C6-C60) aryloxy group Chemical group 0.000 claims description 22
- 125000006752 (C6-C60) arylthio group Chemical group 0.000 claims description 22
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 22
- 125000006820 (C1-C60) alkylthio group Chemical group 0.000 claims description 21
- 230000000903 blocking effect Effects 0.000 claims description 21
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 20
- 125000005368 heteroarylthio group Chemical group 0.000 claims description 20
- 125000005561 phenanthryl group Chemical group 0.000 claims description 19
- 125000004429 atom Chemical group 0.000 claims description 16
- 150000002431 hydrogen Chemical group 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 125000001725 pyrenyl group Chemical group 0.000 claims description 16
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 15
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 15
- 125000006750 (C7-C60) arylalkyl group Chemical group 0.000 claims description 13
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 13
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 13
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 13
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 13
- 125000006754 (C2-C60) heteroarylalkyl group Chemical group 0.000 claims description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 125000004414 alkyl thio group Chemical group 0.000 claims description 12
- 125000003943 azolyl group Chemical group 0.000 claims description 12
- 125000005605 benzo group Chemical group 0.000 claims description 12
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 12
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 12
- 125000004076 pyridyl group Chemical group 0.000 claims description 12
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 11
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 11
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 11
- 125000002971 oxazolyl group Chemical group 0.000 claims description 11
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 11
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 11
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 11
- KLSJWNVTNUYHDU-UHFFFAOYSA-N Amitrole Chemical group NC1=NC=NN1 KLSJWNVTNUYHDU-UHFFFAOYSA-N 0.000 claims description 10
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 claims description 10
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 10
- 125000002883 imidazolyl group Chemical group 0.000 claims description 10
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 9
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 9
- 125000001041 indolyl group Chemical group 0.000 claims description 9
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical group C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims description 8
- 125000003518 norbornenyl group Chemical group C12(C=CC(CC1)C2)* 0.000 claims description 8
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims description 8
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 8
- 229910052723 transition metal Inorganic materials 0.000 claims description 8
- 150000003624 transition metals Chemical class 0.000 claims description 8
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical group C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims description 7
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical group C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 claims description 7
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 7
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 7
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 7
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 7
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 7
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- 125000004306 triazinyl group Chemical group 0.000 claims description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- WIUZHVZUGQDRHZ-UHFFFAOYSA-N [1]benzothiolo[3,2-b]pyridine Chemical group C1=CN=C2C3=CC=CC=C3SC2=C1 WIUZHVZUGQDRHZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 6
- 125000002720 diazolyl group Chemical group 0.000 claims description 6
- 125000003914 fluoranthenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC=C4C1=C23)* 0.000 claims description 6
- 125000004857 imidazopyridinyl group Chemical group N1C(=NC2=C1C=CC=N2)* 0.000 claims description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 6
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 6
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 6
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 6
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 claims description 6
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 claims description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000000335 thiazolyl group Chemical group 0.000 claims description 6
- 125000001425 triazolyl group Chemical group 0.000 claims description 6
- 239000000872 buffer Substances 0.000 claims description 5
- IYYZUPMFVPLQIF-ALWQSETLSA-N dibenzothiophene Chemical group C1=CC=CC=2[34S]C3=C(C=21)C=CC=C3 IYYZUPMFVPLQIF-ALWQSETLSA-N 0.000 claims description 5
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 claims description 5
- 229920001184 polypeptide Polymers 0.000 claims description 5
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 5
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 5
- 239000010948 rhodium Substances 0.000 claims description 5
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical group C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
- TXCDCPKCNAJMEE-UHFFFAOYSA-N dibenzofuran Chemical group C1=CC=C2C3=CC=CC=C3OC2=C1 TXCDCPKCNAJMEE-UHFFFAOYSA-N 0.000 claims description 4
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 4
- 239000010936 titanium Substances 0.000 claims description 4
- BPMFPOGUJAAYHL-UHFFFAOYSA-N 9H-Pyrido[2,3-b]indole Chemical group C1=CC=C2C3=CC=CC=C3NC2=N1 BPMFPOGUJAAYHL-UHFFFAOYSA-N 0.000 claims description 3
- PFWJFKBTIBAASX-UHFFFAOYSA-N 9h-indeno[2,1-b]pyridine Chemical group C1=CN=C2CC3=CC=CC=C3C2=C1 PFWJFKBTIBAASX-UHFFFAOYSA-N 0.000 claims description 3
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical group C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims description 3
- 229910052741 iridium Inorganic materials 0.000 claims description 3
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- ODIRBFFBCSTPTO-UHFFFAOYSA-N 1,3-selenazole Chemical group C1=C[se]C=N1 ODIRBFFBCSTPTO-UHFFFAOYSA-N 0.000 claims description 2
- LPHIYKWSEYTCLW-UHFFFAOYSA-N 1h-azaborole Chemical group N1B=CC=C1 LPHIYKWSEYTCLW-UHFFFAOYSA-N 0.000 claims description 2
- 229910052693 Europium Inorganic materials 0.000 claims description 2
- 229910052771 Terbium Inorganic materials 0.000 claims description 2
- 229910052775 Thulium Inorganic materials 0.000 claims description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052735 hafnium Inorganic materials 0.000 claims description 2
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims description 2
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052762 osmium Inorganic materials 0.000 claims description 2
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 2
- OHENQANLQNOMAO-UHFFFAOYSA-N oxaborole Chemical group O1B=CC=C1 OHENQANLQNOMAO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 229910052703 rhodium Inorganic materials 0.000 claims description 2
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 2
- VSZWPYCFIRKVQL-UHFFFAOYSA-N selanylidenegallium;selenium Chemical compound [Se].[Se]=[Ga].[Se]=[Ga] VSZWPYCFIRKVQL-UHFFFAOYSA-N 0.000 claims description 2
- MABNMNVCOAICNO-UHFFFAOYSA-N selenophene Chemical group C=1C=C[se]C=1 MABNMNVCOAICNO-UHFFFAOYSA-N 0.000 claims description 2
- GZCRRIHWUXGPOV-UHFFFAOYSA-N terbium atom Chemical compound [Tb] GZCRRIHWUXGPOV-UHFFFAOYSA-N 0.000 claims description 2
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims description 2
- FRNOGLGSGLTDKL-UHFFFAOYSA-N thulium atom Chemical compound [Tm] FRNOGLGSGLTDKL-UHFFFAOYSA-N 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- PMJHHCWVYXUKFD-UHFFFAOYSA-N pentadiene group Chemical group C=CC=CC PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 claims 1
- 239000000463 material Substances 0.000 description 24
- 239000002019 doping agent Substances 0.000 description 15
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- 238000000151 deposition Methods 0.000 description 14
- 150000003254 radicals Chemical class 0.000 description 13
- 230000015572 biosynthetic process Effects 0.000 description 11
- 238000003786 synthesis reaction Methods 0.000 description 11
- 229940125904 compound 1 Drugs 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000008021 deposition Effects 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 239000000758 substrate Substances 0.000 description 9
- 238000004770 highest occupied molecular orbital Methods 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 7
- 238000000576 coating method Methods 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- 238000000816 matrix-assisted laser desorption--ionisation Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- 229910052698 phosphorus Inorganic materials 0.000 description 6
- 229920000767 polyaniline Polymers 0.000 description 6
- 238000004528 spin coating Methods 0.000 description 6
- 238000000295 emission spectrum Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 238000001771 vacuum deposition Methods 0.000 description 5
- BNRDGHFESOHOBF-UHFFFAOYSA-N 1-benzoselenophene Chemical group C1=CC=C2[se]C=CC2=C1 BNRDGHFESOHOBF-UHFFFAOYSA-N 0.000 description 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 239000011575 calcium Substances 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 229940125782 compound 2 Drugs 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 125000004957 naphthylene group Chemical group 0.000 description 4
- 125000005562 phenanthrylene group Chemical group 0.000 description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 4
- 150000003852 triazoles Chemical group 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 3
- LVYRSGAIQRZDQS-UHFFFAOYSA-N C1=CC=C2BCCC2=C1 Chemical group C1=CC=C2BCCC2=C1 LVYRSGAIQRZDQS-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000001072 heteroaryl group Chemical group 0.000 description 3
- 238000004128 high performance liquid chromatography Methods 0.000 description 3
- 150000002460 imidazoles Chemical class 0.000 description 3
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 230000000737 periodic effect Effects 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
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- 238000010992 reflux Methods 0.000 description 3
- 239000002356 single layer Substances 0.000 description 3
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical group C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N 1-Heptene Chemical group CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 2
- OBAJPWYDYFEBTF-UHFFFAOYSA-N 2-tert-butyl-9,10-dinaphthalen-2-ylanthracene Chemical compound C1=CC=CC2=CC(C3=C4C=CC=CC4=C(C=4C=C5C=CC=CC5=CC=4)C4=CC=C(C=C43)C(C)(C)C)=CC=C21 OBAJPWYDYFEBTF-UHFFFAOYSA-N 0.000 description 2
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- IKJFYINYNJYDTA-UHFFFAOYSA-N dibenzothiophene sulfone Chemical group C1=CC=C2S(=O)(=O)C3=CC=CC=C3C2=C1 IKJFYINYNJYDTA-UHFFFAOYSA-N 0.000 description 1
- ZOCHARZZJNPSEU-UHFFFAOYSA-N diboron Chemical compound B#B ZOCHARZZJNPSEU-UHFFFAOYSA-N 0.000 description 1
- 229940060296 dodecylbenzenesulfonic acid Drugs 0.000 description 1
- 238000001194 electroluminescence spectrum Methods 0.000 description 1
- 125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical group C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 150000002220 fluorenes Chemical group 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 230000005283 ground state Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 238000004896 high resolution mass spectrometry Methods 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 125000005597 hydrazone group Chemical group 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- LNJXVUXPFZKMNF-UHFFFAOYSA-K iridium(3+);trichloride;trihydrate Chemical compound O.O.O.Cl[Ir](Cl)Cl LNJXVUXPFZKMNF-UHFFFAOYSA-K 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- UVEAFTFQMHUWEY-UHFFFAOYSA-N methane;1,2,4,5-tetrafluoro-3,6-dioxocyclohexane-1,2,4,5-tetracarbonitrile Chemical compound C.C.N#CC1(F)C(=O)C(F)(C#N)C(F)(C#N)C(=O)C1(F)C#N UVEAFTFQMHUWEY-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 1
- BLFVVZKSHYCRDR-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-2-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-2-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C=CC=CC2=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC=CC3=CC=2)C=C1 BLFVVZKSHYCRDR-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 1
- UMRZSTCPUPJPOJ-KNVOCYPGSA-N norbornane Chemical group C1C[C@H]2CC[C@@H]1C2 UMRZSTCPUPJPOJ-KNVOCYPGSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 238000005457 optimization Methods 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 125000005581 pyrene group Chemical group 0.000 description 1
- 125000005548 pyrenylene group Chemical group 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 150000003967 siloles Chemical group 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- YGNGABUJMXJPIJ-UHFFFAOYSA-N thiatriazole Chemical group C1=NN=NS1 YGNGABUJMXJPIJ-UHFFFAOYSA-N 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 1
- 229910001930 tungsten oxide Inorganic materials 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
Disclosed are an organometallic compound, an organic light emitting device including the same, and a light emitting device including the sameAn electronic device of an organic light emitting device. The organometallic compound is represented by formula 1, wherein Ln 1 Ln is a ligand represented by formula 1A 2 Is a ligand represented by formula 1B, n1 is 1 or 2, and n2 is 1 or 2, wherein ring CY 1 And a ring CY 2 Each independently is C 5 ‑C 30 Carbocyclic group or C 1 ‑C 30 Heterocyclic groups, cyclic CY 41 Is a phenyl group, a cyclic CY 42 Is a 5-membered aromatic heterocyclic group, X 1 Is C or N, X 2 Is C or N, Y 1 O, S, se, C (R) 3 )(R 4 )、N(R 3 ) Or B (R) 3 ) And R is 1 ‑R 4 、R 10 、R 20 、R 31 ‑R 34 、R 40 B10, b20 and b40 are as described herein. 1M 1 (Ln 1 ) n1 (Ln 2 ) n2 
Description
Cross reference to related applications
The present application is based on korean patent application No.10-2021-0141368 filed at 2021, 10-21 and korean patent application No. 10-2022-013734 filed at 2022, 10-14, and claims priority and ownership rights thereto, the contents of which are incorporated herein by reference in their entirety.
Technical Field
The present disclosure relates to an organometallic compound, an organic light emitting device including the same, and an electronic apparatus including the organic light emitting device.
Background
An Organic Light Emitting Device (OLED) is a self-emission device having improved characteristics in terms of viewing angle, response time, luminance, driving voltage, and response speed. In addition, OLEDs can produce full color images.
In an example, an organic light emitting device includes an anode, a cathode, and an organic layer disposed between the anode and the cathode. The organic layer includes an emissive layer. The hole transport region may be disposed between the anode and the emission layer, and the electron transport region may be disposed between the emission layer and the cathode. Holes provided from the anode may move toward the emission layer through the hole transport region, and electrons provided from the cathode may move toward the emission layer through the electron transport region. Holes and electrons recombine in the emissive layer to generate excitons. These excitons transition from an excited state to a ground state, thereby generating light.
Disclosure of Invention
Provided are novel organometallic compounds, organic light emitting devices including the same, and electronic devices including the organic light emitting devices.
Additional aspects will be set forth in part in the description which follows, and in part will be obvious from the description, or may be learned by practice of the presented embodiments of the disclosure.
According to one aspect of the embodiments, there is provided an organometallic compound represented by formula 1:
1 (1)
M 1 (Ln 1 ) n1 (Ln 2 ) n2 。
Wherein, the liquid crystal display device comprises a liquid crystal display device,
M 1 in the case of a transition metal, the transition metal,
Ln 1 is a ligand represented by the formula 1A,
Ln 2 is a ligand represented by the formula 1B,
n1 is 1 or 2, and
n2 is 1 or 2 and is preferably selected from the group consisting of,
wherein, in the formulas 1A and 1B,
ring CY 1 And a ring CY 2 Each independently is C 5 -C 30 Carbocyclic group or C 1 -C 30 A heterocyclic group which is a heterocyclic group,
ring CY 41 Is a group of benzene, and is a group of benzene,
ring CY 42 Is a 5-membered aromatic heterocyclic group,
X 1 is C or N, and X 2 Is C or N, and is not limited to the above,
Y 1 o, S, se, C (R) 3 )(R 4 )、N(R 3 ) Or B (R) 3 )，
R 1 -R 4 、R 10 、R 20 、R 31 -R 34 And R 40 Each independently is hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 Hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 1 -C 60 Alkylthio, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 7 -C 60 Alkylaryl, substituted or unsubstituted C 7 -C 60 Arylalkyl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 Alkyl heteroaryl, substituted or unsubstituted C 2 -C 60 Heteroarylalkyl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 Heteroarylthio, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si (Q) 1 )(Q 2 )(Q 3 )、-Ge(Q 1 )(Q 2 )(Q 3 )、-N(Q 4 )(Q 5 )、-B(Q 6 )(Q 7 )、-P(Q 8 )(Q 9 ) or-P (=O) (Q 8 )(Q 9 )，
Multiple R' s 10 Optionally linked together to form a substituted or unsubstituted C 5 -C 30 Carbocyclic groups or substituted or unsubstituted C 1 -C 30 A heterocyclic group which is a heterocyclic group,
multiple R' s 20 Optionally linked together to form a substituted or unsubstituted C 5 -C 30 Carbocyclic groups or substituted or unsubstituted C 1 -C 30 A heterocyclic group which is a heterocyclic group,
R 1 -R 4 、R 10 、R 20 、R 31 -R 34 and R 40 Optionally linked together to form a substituted or unsubstituted C 5 -C 30 Carbocyclic groups or substituted or unsubstituted C 1 -C 30 A heterocyclic group which is a heterocyclic group,
b10 and b20 are each independently 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10,
b40 is 0, 1, 2, 3, 4, or 5,
substituted C 5 -C 30 Carbocycle group, substituted C 1 -C 30 Heterocyclic groups, substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 1 -C 60 Alkylthio, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 1 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 7 -C 60 Alkylaryl, substituted C 7 -C 60 Arylalkyl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 Heteroaryl, substituted C 2 -C 60 Alkyl groupHeteroaryl, substituted C 2 -C 60 Heteroarylalkyl, substituted C 1 -C 60 Heteroaryloxy, substituted C 1 -C 60 At least one substituent of the heteroarylthio group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group is:
deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H、-CDH 2 、-CF 3 、-CF 2 H、-CFH 2 Hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, or C 1 -C 60 Alkylthio;
c each substituted by at least one of 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, or C 1 -C 60 Alkylthio: deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H、-CDH 2 、-CF 3 、-CF 2 H、-CFH 2 Hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkylaryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si (Q) 11 )(Q 12 )(Q 13 )、-Ge(Q 11 )(Q 12 )(Q 13 )、-N(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 )、-P(Q 18 )(Q 19 )、-P(＝O)(Q 18 )(Q 19 ) Or a combination thereof;
C 3 -C 10 cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkylaryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group;
c each substituted by at least one of 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkylaryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H、-CDH 2 、-CF 3 、-CF 2 H、-CFH 2 Hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 1 -C 60 Alkylthio, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl group、C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkylaryl, C 7 -C 60 Arylalkyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 2 -C 60 Heteroarylalkyl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si (Q) 21 )(Q 22 )(Q 23 )、-Ge(Q 21 )(Q 22 )(Q 23 )、-N(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 )、-P(Q 28 )(Q 29 )、-P(＝O)(Q 28 )(Q 29 ) Or a combination thereof; or (b)
-Si(Q 31 )(Q 32 )(Q 33 )、-Ge(Q 31 )(Q 32 )(Q 33 )、-N(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 )、-P(Q 38 )(Q 39 ) or-P (=O) (Q 38 )(Q 39 ) A kind of electronic device
Q 1 -Q 9 、Q 11 -Q 19 、Q 21 -Q 29 And Q 31 -Q 39 Each independently is hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 Hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 1 -C 60 Alkylthio, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted orUnsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 7 -C 60 Alkylaryl, substituted or unsubstituted C 7 -C 60 Arylalkyl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 Alkyl heteroaryl, substituted or unsubstituted C 2 -C 60 Heteroarylalkyl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 Heteroarylthio, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group.
According to another aspect, there is provided an organic light emitting device, comprising: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode, wherein the organic layer includes an emission layer, and wherein the organic layer includes at least one organometallic compound represented by formula 1.
The at least one organometallic compound represented by formula 1 may be included in the emission layer of the organic layer, and in this regard, the at least one organometallic compound represented by formula 1 may act as a dopant.
According to yet another aspect, an electronic device comprising the organic light emitting device is provided.
Drawings
The above and other aspects, features, and advantages of some exemplary embodiments of the present disclosure will be apparent from the following detailed description considered in conjunction with fig. 1, fig. 1 shows a schematic cross-sectional view of an organic light-emitting device according to one or more exemplary embodiments.
Detailed Description
Reference will now be made in further detail to exemplary embodiments, examples of which are illustrated in the accompanying drawings, wherein like reference numerals refer to the like elements throughout. In this regard, the present exemplary embodiment may have different forms and should not be construed as limited to the detailed description set forth herein. Accordingly, the exemplary embodiments and others are described below in further detail by referring to the drawings only.
The terminology used herein is for the purpose of describing one or more exemplary embodiments only and is not intended to be limiting. As used herein, the singular forms "a," "an," and "the" are intended to include the plural forms as well, unless the context clearly indicates otherwise. The term "or" means "and/or". As used herein, the term "and/or" includes any and all combinations of one or more of the associated listed items. It will be further understood that the terms "comprises" and/or "comprising," when used in this specification, specify the presence of stated features, regions, integers, steps, operations, elements, and/or components, but do not preclude the presence or addition of one or more other features, regions, integers, steps, operations, elements, components, and/or groups thereof. The expression "at least one of the elements" for example, modifies the entire list of elements when before or after the list of elements without modifying individual elements of the list.
It will be understood that, although the terms first, second, third, etc. may be used herein to describe various elements, components, regions, layers and/or sections, these elements, components, regions, layers and/or sections should not be limited by these terms. These terms are only used to distinguish one element, component, region, layer or section from another element, component, region, layer or section. Thus, a first element, component, region, layer or section discussed below could be termed a second element, component, region, layer or section without departing from the teachings of the present embodiment.
Exemplary embodiments are described herein with reference to cross-sectional illustrations that are schematic illustrations of idealized embodiments. In this way, deviations from the shape of the figures as a result of, for example, manufacturing techniques and/or tolerances, will be expected. Thus, the embodiments described herein should not be construed as limited to the particular shapes of regions as illustrated herein but are to include deviations in shapes that result, for example, from manufacturing. For example, an area illustrated or described as flat may typically have rough and/or nonlinear features. Moreover, the sharp corners illustrated may be rounded. Accordingly, the regions illustrated in the figures are schematic in nature and their shapes are not intended to illustrate the precise shape of a region and are not intended to limit the scope of the claims.
It will be understood that when an element is referred to as being "on" another element, it can be directly in contact with the other element or intervening elements may be present therebetween. In contrast, when an element is referred to as being "directly on" another element, there are no intervening elements present.
Unless otherwise defined, all terms (including technical and scientific terms) used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this general inventive concept belongs. It will be further understood that terms, such as those defined in commonly used dictionaries, should be interpreted as having a meaning that is consistent with their meaning in the context of the present disclosure and relevant art and will not be interpreted in an idealized or overly formal sense unless expressly so defined herein.
As used herein, work function or Highest Occupied Molecular Orbital (HOMO) energy level is expressed as an absolute value from vacuum energy level. Further, when the work function or HOMO level is referred to as "deep", "high", or "large", the work function or HOMO level has a large absolute value based on a vacuum level of "0 electron volts (eV)", and when the work function or HOMO level is referred to as "shallow", "low", or "small", the work function or HOMO level has a small absolute value based on a vacuum level of "0 eV".
As used herein, "about" or "approximately" includes the stated values and is meant to be within an acceptable range of deviation from the particular values as determined by one of ordinary skill in the art in view of the measurements in question and the errors associated with the measurement of the particular quantities (i.e., limitations of the measurement system). For example, "about" may mean within one or more standard deviations, or within + -10% or 5%, of the stated values.
One aspect of the present disclosure provides an organometallic compound represented by formula 1:
1 (1)
M 1 (Ln 1 ) n1 (Ln 2 ) n2
Wherein in formula 1M 1 Is a transition metal.
For example, M 1 May be a first row transition metal of the periodic table of elements, a second row transition metal of the periodic table of elements, or a third row transition metal of the periodic table of elements.
In one or more embodiments, M 1 May be iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm), or rhodium (Rh).
In one or more embodiments, M 1 May be Ir, pt, os, or Rh.
In one or more embodiments, M 1 May be Ir.
In formula 1, n1 is 1 or 2, and n2 is 1, 2, or 3. For example, in one or more embodiments, n1 and n2 may each be independently 1 or 2.
In one or more embodiments, the sum of n1 and n2 may be 2 or 3.
In one or more embodiments, M 1 Can be Ir, and the sum of n1 and n2 can be 3.
In one or more embodiments, M 1 May be Pt, and the sum of n1 and n2 may be 2.
In formula 1, ln 1 Is a ligand represented by formula 1A:
1A
In formula 1A, X 1 Is C or N, and X 2 Is C or N.
In formula 1A, the ring CY 1 And a ring CY 2 Each independently is C 5 -C 30 Carbocyclic group or C 1 -C 30 A heterocyclic group.
In one or more embodiments, the cyclic CY 1 Can be i) a first ring, ii) a second ring, iii) a fused ring group in which two or more first rings are fused to each other, iv) a fused ring group in which two or more second rings are fused to each other, or v) a fused ring group in which at least one first ring is fused to at least one second ring,
the first ring may be a cyclopentane group, a cyclopentadiene group, a furan group, a thiophene group, a pyrrole group a silol group, an indene group, a benzofuran group, a benzothiophene group, an indole group, a benzothiophene group, a benzoxazole group,
An azole group, iso->
Azole group,/->
Diazole group, i->
Diazole groups, (-)>
Triazole group, iso->
Triazole groups, thiazole groups, isothiazole groups, thiadiazole groups, isothiadiazole groups, thiatriazole groups, isothiatriazole groups, pyrazole groups, imidazole groups, triazole groups, tetrazole groups, azasilole groups, diazasilole groups, or triazasilole groups, and
The second ring may be an adamantyl group, norbornane group, norbornene group, cyclohexane group, cyclohexene group, phenyl group, pyridine group, pyrimidine group, pyrazine group, pyridazine group, or triazine group.
In one or more embodiments, the cyclic CY 1 And a ring CY 2 Can each independently be a cyclopentane group, a cyclohexane group, a cycloheptane group, a cyclopentene group, a cyclohexene group, a cycloheptene group, a phenyl group, a naphthalene group, an anthracene group, a phenanthrene group, a benzo [9,10 ]]A phenanthrene group, a pyrene group,
A group, a cyclopentadienyl group, a 1,2,3, 4-tetrahydronaphthyl group, a thienyl group, a furanyl group, an indolyl group, a benzoborolane group, a benzophospholane group, an indenyl group, a benzothiophene group, a benzosilol group, a benzoguanamine group a benzogermanopyranadiene group, a benzothiophene group, a benzoselenophene group, a benzofuran group, a carbazole group, a dibenzoborolane group, a dibenzophospholane group, a benzoselenophene group, a benzofurane group, a benzoborolane group, a benzoselenophene group, a benzofurane group, a benzoborolane group, a benzoselenophene group, a benzo fluorene group, dibenzosilole group, dibenzogermanium heterocyclopentadiene group, dibenzothiophene group, dibenzoselenophene group, dibenzofuran group, dibenzothiophene 5-oxide group, 9H-fluorene-9-one group, dibenzothiophene 5, 5-dioxide group, azaindole group, azabenzoborolan group, azabenzophosphinopentadiene group, azaindene group Azabenzosilole groups, azabenzogermanium heterocyclopentadiene groups, azabenzothiophene groups, azabenzoselenophene groups, azabenzofuran groups, azacarbazole groups, azadibenzoborole groups, azadibenzophosphole groups, azafluorene groups, azadibenzosilole groups, azadibenzogermanium heterocyclopentadiene groups, azadibenzothiophene groups, azadibenzoselenophene groups, azadibenzofuran groups, azadibenzothiophene 5-oxide groups, aza-9H-fluoren-9-one groups, azadibenzothiophene 5, 5-dioxide groups, pyridine groups, pyrimidine groups, pyrazine groups, pyridazine groups, triazine groups, quinoline groups, isoquinoline groups, quinoxaline groups, quinazoline groups, phenanthroline groups, triazine groups, quinoline groups, pyrrole groups, pyrazole groups, imidazole groups, triazole groups,/o >
Azole radical, iso
An azole group, a thiazole group, an isothiazole group,/-thiazole group>
Diazole group, thiadiazole group, benzopyrazole group, benzimidazole group, benzo +.>
An azole group, a benzothiazole group, a benzo +.>
An diazole group, a benzothiadiazole group, a 5,6,7, 8-tetrahydroisoquinoline group, or a 5,6,7, 8-tetrahydroquinoline group.
In one or more embodiments, the cyclic CY 1 And a ring CY 2 And may each independently be a phenyl group, a naphthalene group, a 1,2,3, 4-tetrahydronaphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyrazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a benzofuran group, a benzothiophene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, or an azadibenzothiophene group.
In one or more embodiments, the cyclic CY 1 May be a pyridine group, pyrimidine group, pyrazine group, triazine group, quinoline group, isoquinoline group, quinoxaline group, or quinazoline group.
In one or more embodiments, the cyclic CY 2 Can be a phenyl group, a naphthalene group, a pyridine group, a pyrimidine group, a pyrazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, or a dibenzothiophene group.
In one or more embodiments, formula 1A isRing CY 1 Can be represented by one of formulas 1-1 to 1-16:
in formulas 1-1 to 1-16,
R 11 -R 14 can be each independently as R 10 As described and may each be other than hydrogen, and
* Representation and M 1 And represents a binding site to an adjacent atom.
In one or more embodiments, the ring CY in formula 1A 2 Can be represented by one of formulas 2-1 to 2-16:
in formulas 2-1 to 2-16,
R 21 -R 24 can be each independently as for R 20 Described and may each be other than hydrogen, and
* Representation and M 1 And "indicates the binding site to an adjacent atom.
In formula 1, ln 2 Is a ligand represented by formula 1B:
1B of the formula
Wherein, in the formula 1B,
ring CY 41 Is phenyl groupA mass, and
ring CY 42 Is a 5 membered aromatic heterocyclic group.
In one or more embodiments, the cyclic CY 42 Can be furan group, thiophene group, selenophene group, pyrrole group, boro-heterocyclopentadiene group, or the like, 
An azole group, a thiazole group, a selenazole group, an imidazole group, an azaborole group, an oxaborole group, a thiaborole group, a selenoboropentadiene group, or a diboron (diborole) group.
In one or more embodiments, the formula 1B is defined by
The part represented may be composed of
One of the formulas 3-1 to 3-16:
in formulas 3-1 to 3-16,
R 31 -R 34 may each independently be as described herein, and may each be other than hydrogen, and
* Representation and M 1 And represents a binding site to an adjacent atom.
In formula 1, R 1 -R 4 、R 10 、R 20 、R 31 -R 34 And R 40 Each independently is hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 Hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy group,Substituted or unsubstituted C 1 -C 60 Alkylthio, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 7 -C 60 Alkylaryl, substituted or unsubstituted C 7 -C 60 Arylalkyl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 Alkyl heteroaryl, substituted or unsubstituted C 2 -C 60 Heteroarylalkyl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 Heteroarylthio, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -N (Q) 1 )(Q 2 )、-Si(Q 3 )(Q 4 )(Q 5 )、-Ge(Q 3 )(Q 4 )(Q 5 )、-B(Q 6 )(Q 7 )、-P(Q 8 )(Q 9 ) or-P (=O) (Q 8 )(Q 9 )。
In formula 1A, b10 and b20 are each independently 1, 2, 3, 4, 5, 6, 7, 8, 9, or 10.
In one or more embodiments, b10 and b20 can each independently be 1, 2, 3, 4, 5, 6, 7, or 8.
In one or more embodiments, b10 and b20 can each independently be 1, 2, 3, or 4.
In one or more embodiments, b10 and b20 may each independently be 1 or 2.
In one or more embodiments, b10 and b20 may each independently be 1.
In formula 1B, B40 is 0, 1, 2, 3, 4, or 5.
In one or more embodiments, b40 may be 1, 2, 3, 4, or 5.
In one or more embodiments, b40 may be 1, 2, 3, or 4.
In one or more embodiments, b40 may be 1, 2, or 3.
In one or more embodiments, b40 may be 1 or 2.
In one or more embodiments, b40 may be 1.
In one or more embodiments, R 1 -R 4 、R 10 、R 20 、R 31 -R 34 And R 40 Each independently can be:
hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H、-CDH 2 、-CF 3 、-CF 2 H、-CFH 2 Hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, or C 1 -C 20 Alkylthio;
c each substituted by at least one of 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, or C 1 -C 20 Alkylthio: deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H、-CDH 2 、-CF 3 、-CF 2 H、-CFH 2 Hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C 1 -C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, pyridinyl, pyrimidinyl, or combinations thereof;
cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo [9,10 ] ]Phenanthryl, pyrenyl, and,
A group, a pyrrolyl group, a thienyl group, a furyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, and a +.>
Azolyl, iso->
Oxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, isobenzothiazolyl, benzo->
Azolyl, isobenzo->
Oxazolyl, triazolyl, tetrazolyl, < >>
Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, or imidazopyrimidinyl;
cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo [9,10 ]]Phenanthryl, pyrenyl, and,
A group, a pyrrolyl group, a thienyl group, a furyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, and a +.>
Azolyl, iso->
Oxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, isobenzothiazolyl, benzo- >
Azolyl, isobenzo->
Oxazolyl, triazolyl, tetrazolyl, < >>
Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, or imidazopyrimidinyl: deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H、-CDH 2 、-CF 3 、-CF 2 H、-CFH 2 Hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, C 1 -C 20 Alkylthio, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo [9,10 ]]Phenanthryl, pyrenyl,>
a group, a pyrrolyl group, a thienyl group, a furyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, and a +.>
Azolyl, iso
Oxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, isobenzothiazolyl, benzo- >
Azolyl, isobenzo->
Oxazolyl, triazolyl, tetrazolyl, < >>
Diazolyl, triazinyl, dibenzofuranyl, dibenzothienyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, or a combination thereof; or (b)
-Si(Q 1 )(Q 2 )(Q 3 )、-Ge(Q 1 )(Q 2 )(Q 3 )、-N(Q 4 )(Q 5 )、-B(Q 6 )(Q 7 )、-P(Q 8 )(Q 9 ) or-P (=O) (Q 8 )(Q 9 )。
In one or more embodiments, R 1 -R 4 、R 10 、R 20 、R 31 -R 34 And R 40 Each independently can be:
hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H、-CDH 2 、-CF 3 、-CF 2 H、-CFH 2 、C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, or C 1 -C 20 Alkylthio; or (b)
A group represented by one of formulas 9-1 to 9-61, 9-201 to 9-237, 10-1 to 10-129, or 10-201 to 10-350:
in formulas 9-1 to 9-61, 9-201 to 9-237, 10-1 to 10-129, and 10-201 to 10-350, the expression "Ph" represents a binding site to an adjacent atom, the expression "TMS" represents a trimethylsilyl group, and the expression "TMG" represents a trimethylgermyl group.
In one or more embodiments, R 10 、R 20 And R 31 -R 34 At least one of (C) may be deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H、-CDH 2 、-CF 3 、-CF 2 H、-CFH 2 、C 1 -C 60 Alkyl, or C substituted by at least one deuterium 1 -C 60 An alkyl group.
In formulas 1A and 1B, a plurality of R 10 Optionally linked together to form a substituted or unsubstituted C 5 -C 30 Carbocyclic groups or substituted or unsubstituted C 1 -C 30 A heterocyclic group; multiple R' s 20 Optionally linked together to form a substituted or unsubstituted C 5 -C 30 Carbocyclic groups or substituted or unsubstituted C 1 -C 30 A heterocyclic group; r is as follows 1 -R 4 、R 10 、R 20 、R 31 -R 34 And R 40 Optionally linked together to form a substituted or unsubstituted C 5 -C 30 Carbocyclic groups or substituted or unsubstituted C 1 -C 30 A heterocyclic group. As used herein, "R 1 -R 4 、R 10 、R 20 、R 31 -R 34 And R 40 Optionally linked together to form a substituted or unsubstituted C 5 -C 30 Carbocyclic groups or substituted or unsubstituted C 1 -C 30 The heterocyclic group "excludes the following: (1) Multiple R' s 10 Optionally linked together to form a substituted or unsubstituted C 5 -C 30 Carbocyclic groups or substituted or unsubstituted C 1 -C 30 A heterocyclic group; (2) Multiple R' s 20 Optionally linked together to form a substituted or unsubstituted C 5 -C 30 Carbocyclic groups or substituted or unsubstituted C 1 -C 30 A heterocyclic group; and (3) a plurality of R 40 Optionally linked together to form a substituted or unsubstituted C 5 -C 30 Carbocyclic groups or substituted or unsubstituted C 1 -C 30 A heterocyclic group.
In one or more embodiments, in formulas 1A and 1B, a plurality of R 10 Is a single unit, and is a single unit; multiple R' s 20 Is a single unit, and is a single unit; or R is 1 -R 4 、R 10 、R 20 、R 31 -R 34 And R 40 Optionally linked together to form a substituted or unsubstituted C 5 -C 30 Carbocyclic groups or substituted or unsubstituted C 1 -C 30 A heterocyclic group.
In one or more embodiments, a plurality of R 10 Is a single unit, and is a single unit; multiple R' s 20 Is a single unit, and is a single unit; or R is 1 -R 4 、R 10 、R 20 、R 31 -R 34 And R 40 Optionally linked together via a single bond, a double bond, or a first linking group to form a group that is unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 Carbocyclic groups, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Heterocyclic groups (e.g. each unsubstituted or substituted with at least one R 10a Substituted fluorene groups, xanthene groups, acridine groups, etc.). R is R 10a Can be as for R 10 Described.
The first linking group may be a group of the formula-N (R 8 )-*'、*-B(R 8 )-*'、*-P(R 8 )-*'、*-C(R 8 )(R 9 )-*'、*-Si(R 8 )(R 9 )-*'、*-Ge(R 8 )(R 9 )-*'、*-S-*'、*-Se-*'、*-O-*'、*-C(＝O)-*'、*-S(＝O)-*'、*-S(＝O) 2 -*'、*-C(R 8 )＝*'、*＝C(R 8 )-*'、*-C(R 8 )＝C(R 9 ) -, x'; -C (=s) -, x or-c≡c-, R is R 8 And R is 9 Can be each independently as for R 10 As described, and each of the x and x' represent a binding site to an adjacent atom.
In one or more embodiments, Q 1 -Q 9 、Q 11 -Q 19 、Q 21 -Q 29 And Q 31 -Q 39 Each independently can be:
deuterium, -CH 3 、-CD 3 、-CD 2 H、-CDH 2 、-CH 2 CH 3 、-CH 2 CD 3 、-CH 2 CD 2 H、-CH 2 CDH 2 、-CHDCH 3 、-CHDCD 2 H、-CHDCDH 2 、-CHDCD 3 、-CD 2 CD 3 、-CD 2 CD 2 H. or-CD 2 CDH 2 ；
N-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl; or (b)
N-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl, or naphthyl each substituted with at least one of: deuterium, C 1 -C 10 Alkyl, phenyl, or a combination thereof.
In one or more embodiments, ln 2 Can be represented by one of formulas 11-1 to 11-3:
in the formulae 11-1 to 11-3,
R 1 、R 2 、R 31 -R 34 、R 40 、CY 42 and Y 1 As may be described herein separately,
b41 may be 1, 2, or 3,
R 41 and R is 44 Can be each independently as for R 40 Described, and
* And' each represents a group corresponding to M 1 Is a binding site for a polypeptide.
In one or more embodiments, ln 2 Can be represented by one of formulas 21-1 to 21-6:
in formulas 21-1 to 21-6,
R 1 、R 2 、R 31 -R 34 and Y 1 Can be respectively as described hereinAs described in the foregoing,
X 41 can be N, B, or C (R) 46 )，
X 42 Can be O, S, se, N (R) 47 ) Or B (R) 47 )，
R 41 -R 47 Can be each independently as for R 40 Described, and
* And' each represents a group corresponding to M 1 Is a binding site for a polypeptide.
In one or more embodiments, the organometallic compound may be a compound represented by one of formulas 31-1 to 31-6:
in the formulae 31-1 to 31-6, M 1 、n1、n2、Y 1 、R 1 And R is 2 As may be described herein separately,
X 11 can be C (R) 11 ) Or N, X 12 Can be C (R) 12 ) Or N, X 13 Can be C (R) 13 ) Or N, and X 14 Can be C (R) 14 ) Or N, or a combination of two,
X 21 Can be C (R) 21 ) Or N, X 22 Can be C (R) 22 ) Or N, X 23 Can be C (R) 23 ) Or N, and X 24 Can be C (R) 24 ) Or N, or a combination of two,
X 41 can be N, B, or C (R) 46 )，
X 42 Can be O, S, se, N (R) 47 ) Or B (R) 47 )，
R 11 -R 14 Can be each independently as for R 10 As described in the description of the present invention,
R 21 -R 24 can be each independently as for R 20 As described in the description of the present invention,
R 31 -R 34 each independently as described herein,
R 43 -R 47 can be each independently as for R 40 As described in the description of the present invention,
R 11 -R 14 optionally linked together to form a group which is unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 Carbocyclic groups, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 A heterocyclic group which is a heterocyclic group,
R 21 -R 24 optionally linked together to form a group which is unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 Carbocyclic groups, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 A heterocyclic group which is a heterocyclic group,
R 31 -R 34 optionally linked together to form a group which is unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 Carbocyclic groups, either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 A heterocyclic group, and
R 10a can be as for R 10 Described.
C 5 -C 30 Carbocycle group and C 1 -C 30 The heterocyclic groups may each be as described herein.
In one or more embodiments, "unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 Examples of heterocyclic groups "include groups each unsubstituted or substituted with at least one R 10a Substituted phenyl groups, naphthyl groups, cyclopentane groups, cyclopentadienyl groups, cyclohexane groups, cycloheptane groups, bicyclo [2.2.1 ]]A heptyl group, a furan group, a thiophene group, a pyrrole group, a silole group, an indene group, a benzofuran group, a benzothiophene group, an indole group, or a benzothiophene group. R is R 10a Can be as forR 10 Described.
In one or more embodiments, R is present in an amount b10 10 R in the amount of b20 20 、R 31 -R 34 R in the quantity b40 40 、R 41 And R 42 Can be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, 2-methylbutyl, sec-pentyl, tert-pentyl, neopentyl, 3-pentyl, 3-methyl-2-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, phenyl, biphenyl, (C) 1 -C 20 Alkyl) phenyl, -naphthyl, -Si (Q) 1 )(Q 2 )(Q 3 ) or-Ge (Q) 1 )(Q 2 )(Q 3 )。
In one or more embodiments, the ligand represented by formula 1A may include one silyl group or one germyl group, and the ligand represented by formula 1B may not include a silyl group or a germyl group.
In one or more embodiments, the organometallic compound may be one of compounds 1 to 73:
in one or more embodiments, the organometallic compound may be electrically neutral.
The organometallic compound represented by formula 1 may satisfy the structure of formula 1 as follows: wherein the ligand represented by formula 1B includes a ring CY in which a 5-membered aromatic heterocyclic group is condensed 42 Is of the ring CY of (C) 41 A phenyl group. Due to this structure, the organometallic compound represented by formula 1 has excellent light emission characteristics, and has such characteristics as to be suitable for use as a light emitting material having high color purity by controlling an emission wavelength range.
In addition, the organometallic compound represented by formula 1 has excellent electric mobility, and thus, an electronic device including the organometallic compound, for example, an organic light emitting device including the organometallic compound may have a low driving voltage, high efficiency, long lifetime, and exhibit reduced roll-off phenomenon.
In addition, photochemical stability of the organometallic compound represented by formula 1 may be improved, and thus, an electronic device including the organometallic compound, for example, an organic light emitting device may exhibit high emission efficiency, long lifetime, and high color purity.
Evaluation of the Highest Occupied Molecular Orbital (HOMO) level, lowest Unoccupied Molecular Orbital (LUMO) level, singlet (S) of the organometallic compound represented by formula 1 by Density Functional Theory (DFT) by using Gaussian 09 program accompanied with molecular structure optimization obtained at the B3LYP group level 1 ) Energy level, and triplet (T 1 ) Energy levels, and the results thereof are shown in table 1.
TABLE 1
Referring to table 1, it was confirmed that the organometallic compound represented by formula 1 has suitable electrical characteristics for use as a dopant in electronic devices such as organic light emitting devices.
In one or more embodiments, the organometallic compound may have an emission spectrum or a full width at half maximum (FWHM) of an emission peak of an electroluminescent spectrum of about 70 nanometers (nm) or less. For example, the FWHM of the emission spectrum of the organometallic compound or the emission peak of the electroluminescent spectrum may be in the range of about 30nm to about 65nm, about 40nm to about 63nm, or about 45nm to about 62 nm.
In one or more embodiments, the organometallic compound has an emission spectrum or an emission peak of an electroluminescent spectrum having a maximum emission wavelength (emission peak wavelength, λ max ) May be in the range of about 500nm to about 600nm, for example in the range of about 490nm to about 550 nm. For example lambda of the emission spectrum of the organometallic compound or the emission peak of the electroluminescent spectrum max May be in the range of about 500nm to about 540nm, or about 510nm to about 540 nm.
The method of synthesis of the organometallic compound represented by formula 1 can be recognized by one of ordinary skill in the art by reference to the synthetic examples described herein.
Accordingly, the organometallic compound represented by formula 1 may be suitable for use as a dopant in an organic layer, such as an emission layer, of an organic light emitting device. Accordingly, another aspect of the present disclosure provides an organic light emitting device, comprising: a first electrode; a second electrode; and an organic layer disposed between the first electrode and the second electrode and including an emission layer, wherein the organic layer includes at least one organometallic compound represented by formula 1.
As described above, since the organic layer including the organometallic compound represented by formula 1 is included, the organic light emitting device may have excellent characteristics in terms of driving voltage, current efficiency, power efficiency, external quantum efficiency, lifetime, and/or color purity. Moreover, such organic light emitting devices may have reduced roll-off phenomena and relatively narrow FWHM of emission peaks in the Electroluminescence (EL) spectrum.
The organometallic compound represented by formula 1 may be used between an electrode pair of the organic light emitting device. For example, an organometallic compound represented by formula 1 may be included in the emission layer. In this regard, the organometallic compound may act as a dopant, and the emission layer may further include a host (i.e., the amount of organometallic compound represented by formula 1 in the emission layer is less than the amount of host included in the emission layer).
In one or more embodiments, the emission layer may emit green light. For example, the emissive layer may emit green light having a maximum emission wavelength in the range of about 500nm to about 600nm, such as in the range of about 490nm to about 550 nm.
The expression "(organic layer) as used herein includes a case where" (organic layer) includes at least one kind of organometallic compound represented by formula 1 "may include a case where" (organic layer) includes the same organometallic compound represented by formula 1 "and a case where" (organic layer) includes two or more different organometallic compounds represented by formula 1 ".
In one or more embodiments, the organic layer may include only compound 1 as the organometallic compound. In this embodiment, compound 1 may be included in the emission layer of the organic light emitting device. In one or more embodiments, the organic layer may include compound 1 and compound 2 as the organometallic compound. In this embodiment, compound 1 and compound 2 may be present in the same layer (e.g., compound 1 and compound 2 may all be present in the emissive layer).
The first electrode may be an anode as a hole injection electrode, and the second electrode may be a cathode as an electron injection electrode; or the first electrode may be a cathode as an electron injection electrode and the second electrode may be an anode as a hole injection electrode.
In one or more embodiments, in the organic light emitting device, the first electrode may be an anode, the second electrode may be a cathode, and the organic layer may further include a hole transport region between the first electrode and the emission layer and an electron transport region between the emission layer and the second electrode, wherein the hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof, and the electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.
The term "organic layer" as used herein refers to a single layer or multiple layers disposed between a first electrode and a second electrode of an organic light emitting device. In addition to organic compounds, the "organic layer" may also include organometallic complexes comprising metals.
Fig. 1 is a schematic cross-sectional view of an organic light emitting device 10 according to one or more embodiments. Hereinafter, a structure and a manufacturing method of the organic light emitting device 10 according to one or more embodiments of the present disclosure will be described with respect to fig. 1. The organic light emitting device 10 includes a first electrode 11, an organic layer 15, and a second electrode 19 sequentially stacked.
The substrate may additionally be arranged below the first electrode 11 or above the second electrode 19. For use as the substrate, any substrate usable in the art for use in an organic light emitting device may be used, and the substrate may be a glass substrate or a transparent plastic substrate each having excellent mechanical strength, thermal stability, transparency, surface smoothness, ease of handling, and/or water resistance.
The first electrode 11 may be formed, for example, by depositing or sputtering a material for forming the first electrode 11 on the substrate. The first electrode 11 may be an anode. The material used to form the first electrode 11 may be selected from materials having a high work function to promote hole injection. The first electrode 11 may be a reflective electrode, a semi-transmissive electrode, or a transmissive electrode. In one or more embodiments, the material used to form the first electrode 11 may be Indium Tin Oxide (ITO), indium Zinc Oxide (IZO), tin oxide (SnO) 2 ) Or zinc oxide (ZnO). In one or more embodiments, the material used to form the first electrode 11 may be a metal, such as magnesium (Mg), aluminum (Al), silver (Ag), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag).
The first electrode 11 may have a single-layer structure or a multi-layer structure including two or more layers. For example, the first electrode 11 may have a three-layer structure of ITO/Ag/ITO, but the structure of the first electrode 11 is not limited thereto.
An organic layer 15 is on the first electrode 11.
The organic layer 15 may include: the hole transport region; the emission layer; and the electron transport region.
The hole transport region may be disposed between the first electrode 11 and the emission layer.
The hole transport region may include a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof.
The hole transport region may include only a hole injection layer or a hole transport layer. The hole transport region may have a hole injection layer/hole transport layer structure, or a hole injection layer/hole transport layer/electron blocking layer structure, in which constituent layers of the respective structures are sequentially stacked in the stated order from the first electrode 11.
When the hole transport region includes a hole injection layer, the hole injection layer may be formed on the first electrode 11 by using one or more suitable methods, such as vacuum deposition, spin coating, casting, and/or langmuir-blodgett (LB) deposition.
When the hole injection layer is formed by vacuum deposition, deposition conditions may vary depending on the material used to form the hole injection layer, and the structure and thermal characteristics of the hole injection layer. For example, the deposition conditions may include a deposition temperature in the range of about 100 ℃ to about 500 ℃, at about 10 ° -8 Tray to about 10 -3 Vacuum pressure in the range of the tray, and in the range of about
-about->
A deposition rate in the range of (2). However, the deposition conditions are not limited thereto.
When the hole injection layer is formed by spin coating, coating conditions may vary depending on the material used to form the hole injection layer, as well as the structure and thermal properties of the hole injection layer. For example, the coating conditions may include a coating speed in the range of about 2,000 revolutions per minute (rpm) to about 5,000rpm, and a heat treatment temperature for removing the solvent after coating in the range of about 80 ℃ to about 200 ℃. However, the coating conditions are not limited thereto.
The conditions for forming the hole transport layer and the electron blocking layer may be similar to, or even the same as, the conditions for forming the hole injection layer.
The hole transport region may include at least one of: 4,4',4 "-tris (3-methylphenylphenylamino) triphenylamine (m-MTDATA), 4',4" -tris (N, N-diphenylamino) triphenylamine (TDATA), 4',4 "-tris { N- (2-naphthyl) -N-phenylamino } -triphenylamine (2-TNATA), N, N ' -bis (1-naphthyl) -N, N ' -diphenyl benzidine (NPB), beta-NPB, N ' -bis (3-methylphenyl) -N, N ' -diphenyl- [1, 1-biphenyl ] -4,4' -diamine (TPD), spiro-TPD, spiro-NPB, methylated NPB, 4' -cyclohexylidene bis [ N, N-bis (4-methylphenyl) aniline ] (TAPC), 4' -bis [ N, N ' - (3-tolyl) amino ] -3,3' -dimethylbiphenyl (HMTPD), 4' -tris (N-carbazolyl) triphenylamine (TCTA), polyaniline/dodecylbenzenesulfonic acid (PANI/DBSA), poly (3, 4-ethylenedioxythiophene)/poly (4-sulfostyrene) (PEDOT/PSS), polyaniline/camphorsulfonic acid (PANI/CSA), polyaniline/poly (4-sulfostyrene) (PANI/PSS), and, A compound represented by formula 201, or a compound represented by formula 202:
201, a method for manufacturing a semiconductor device
202, respectively
In formula 201, ar 101 And Ar is a group 102 Each independently can be:
phenylene, pentalene, indenylene, naphthylene, azulene, heptylene, acenaphthylene, fluorenylene, phenalenylene, phenanthrylene, anthrylene, fluoranthenylene, benzo [9,10 ]]Phenanthryl, pyrenyl, and pyrenyl
A group, a tetracene group, a picene group, a perylene group, or a pentacene group; or (b)
Each of which is substituted by at least one of phenylene, pentalene, indenylene, naphthylene, azulenylene, heptylene, acenaphthylene, fluorenylene, phenalenylene, phenanthrylene, anthrylene, fluoranthrylene, benzo [9,10 ]]Phenanthryl, pyrenyl, and pyrenyl
A group, a tetracene group, a picene group, a perylene group, or a pentacene group: deuterium, -F, -Cl, -Br, -I, -SF 5 Hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 1 -C 60 Alkylthio, C 3 -C 10 Cycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkylaryl, C 7 -C 60 Arylalkyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 2 -C 60 A heteroarylalkyl group, a monovalent non-aromatic fused polycyclic group, a monovalent non-aromatic fused heteropolycyclic group, or a combination thereof.
In formula 201, xa and xb may each independently be an integer of 0 to 5, or may each independently be 0, 1, or 2. For example, xa may be 1 and xb may be 0, but is not limited thereto.
In formulas 201 and 202, R 101 -R 108 、R 111 -R 119 And R 121 -R 124 Each independently can be:
hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 Hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C 1 -C 10 Alkyl (e.g., methyl, ethyl, propyl, butyl, pentyl, hexyl, etc.), C 1 -C 10 Alkoxy (e.g., methoxy, ethoxy, propoxy, butoxy, pentoxy, etc.), or C 1 -C 10 Alkylthio;
c each substituted by at least one of 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, or C 1 -C 10 Alkylthio: deuterium, -F, -Cl, -Br, -I, -SF 5 A hydroxyl group, a cyano group, a nitro group, an amino group, an amidino group, a hydrazine group, a hydrazone group, a carboxylic acid group or a salt thereof, a sulfonic acid group or a salt thereof, a phosphoric acid group or a salt thereof, or a combination thereof;
phenyl, naphthyl, anthracyl, fluorenyl, or pyrenyl; or (b)
Phenyl, naphthyl, anthracenyl, fluorenyl, or pyrenyl each substituted with at least one of: deuterium, -F, -Cl, -Br, -I, -SF 5 Hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C 1 -C 10 Alkyl, C 1 -C 10 Alkoxy, C 1 -C 10 Alkylthio, or a combination thereof, embodiments of the present disclosure are not limited thereto.
In formula 201, R 109 The method comprises the following steps:
phenyl, naphthyl, anthracyl, or pyridinyl; or (b)
Phenyl and naphthalene each substituted by at least one ofA group, anthracenyl, or pyridinyl group: deuterium, -F, -Cl, -Br, -I, -SF 5 Hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, C 1 -C 20 Alkylthio, phenyl, naphthyl, anthracenyl, pyridinyl, or a combination thereof.
In one or more embodiments, the compound represented by formula 201 may be represented by formula 201A, but embodiments of the present disclosure are not limited thereto:
201A
Wherein in formula 201A, R 101 、R 111 、R 112 And R 109 Each independently as described herein.
For example, the compound represented by formula 201 and the compound represented by formula 202 may include compounds HT1 to HT20, but embodiments of the present disclosure are not limited thereto:
The hole transport region may have a thickness of about
-about->
For example about->
-about
Within a range of (2). When the hole transport region includes at least one of a hole injection layer and a hole transport layer, the hole injection layer may have a thickness of about +.>
-about->
For example about->
-about->
Within a range of about +.>
-about->
For example about->
-about->
Within a range of (2). When the thicknesses of the hole transport region, the hole injection layer, and the hole transport layer are within these ranges, satisfactory hole transport characteristics can be obtained without a significant increase in driving voltage.
In addition to these materials, the hole transport region may further include a charge generating material to improve conductive properties. The charge generating material may be uniformly or non-uniformly dispersed in the hole transport region.
The charge generating material may be, for example, a p-dopant. The p-dopant may be one of a quinone derivative, a metal oxide, and a cyano group-containing compound, but embodiments of the present disclosure are not limited thereto. Non-limiting examples of the p-dopant are quinone derivatives such as Tetracyanoquinodimethane (TCNQ) or 2,3,5, 6-tetrafluoro-tetracyano-1, 4-benzoquinone dimethane (F4-TCNQ); metal oxides such as tungsten oxide or molybdenum oxide; and cyano group-containing compounds such as the compound HT-D1 or F12, but are not limited thereto:
The hole transport region may include a buffer layer.
Also, the buffer layer may compensate for an optical resonance distance according to a wavelength of light emitted from the emission layer, and thus, efficiency of the formed organic light emitting device may be improved.
The emissive layer may then be formed on the hole transport region by using one or more suitable methods, such as vacuum deposition, spin coating, casting, and/or LB deposition. When the emission layer is formed by vacuum deposition or spin coating, although deposition or coating conditions may vary depending on materials used to form the emission layer, the deposition or coating conditions may be similar to those applied when forming the hole injection layer.
Meanwhile, when the hole transport region includes an electron blocking layer, a material for forming the electron blocking layer may be selected from the materials for the hole transport region described above and a host material to be described later. However, the material for forming the electron blocking layer is not limited thereto. For example, when the hole transport region includes an electron blocking layer, a material for forming the electron blocking layer may be mCP, which will be described below.
The emission layer may include a host and a dopant, and the dopant may include an organometallic compound represented by formula 1.
In one or more embodiments, the body may include at least one of: 1,3, 5-tris (N-phenylbenzimidazol-2-yl) benzene (TPBi), 3-tert-butyl-9, 10-bis (naphthalen-2-yl) anthracene (TBADN), 9, 10-bis (naphthalen-2-yl) anthracene (ADN, also known as "DNA"), 4' -bis (N-carbazolyl) -1,1' -biphenyl (CBP), 4' -bis (9-carbazolyl) -2,2' -dimethyl-biphenyl (CDBP), N ' N "-1, 3, 5-Tricarbazolylbenzene (TCP), 1, 3-bis (carbazol-9-yl) benzene (mCP), compound H50, or compound H51:
in one or more embodiments, the host may further include a compound represented by formula 301:
301
In formula 301 Ar 111 And Ar is a group 112 Each independently can be:
phenylene, naphthylene, phenanthrylene, or pyrenylene; or (b)
Phenylene, naphthylene, phenanthrylene, or pyreylene each substituted with at least one of: phenyl, naphthyl, anthracyl, or a combination thereof.
In formula 301 Ar 113 -Ar 116 Each independently can be:
C 1 -C 10 alkyl, phenyl, naphthyl, phenanthryl, or pyrenyl; or (b)
Phenyl, naphthyl, phenanthryl, or pyrenyl, each substituted with at least one of: phenyl, naphthyl, anthracyl, or a combination thereof.
In formula 301, g, h, i, and j may each independently be an integer of 0 to 4, and for example, may each independently be 0, 1, or 2.
In formula 301 Ar 113 -Ar 116 Each independently can be:
is as followsIs at least one substituted C 1 -C 10 Alkyl: phenyl, naphthyl, anthracyl, or a combination thereof;
phenyl, naphthyl, anthracyl, pyrenyl, phenanthryl, or fluorenyl;
phenyl, naphthyl, anthracenyl, pyrenyl, phenanthrenyl, or fluorenyl each substituted with at least one of: deuterium, -F, -Cl, -Br, -I, -SF 5 Hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 1 -C 60 Alkylthio, phenyl, naphthyl, anthracenyl, pyrenyl, phenanthryl, fluorenyl, or combinations thereof; or (b)
In one or more embodiments, the host can include a compound represented by formula 302:
302, a method of manufacturing a semiconductor device
Wherein in formula 302 Ar 122 -Ar 125 Ar in formula 301 may be each independently as for 113 Described.
In formula 302, ar 126 And Ar is a group 127 Can each independently be C 1 -C 10 Alkyl (e.g., methyl, ethyl, or propyl).
In formula 302, k and l may each independently be an integer from 0 to 4. For example, k and l may each independently be 0, 1, or 2.
When the organic light emitting device 10 is a full-color organic light emitting device, the emission layer may be patterned into a red emission layer, a green emission layer, and a blue emission layer. In one or more embodiments, the emission layer may emit white light based on a stacked structure including a red emission layer, a green emission layer, and/or a blue emission layer, and various modifications are possible.
When the emission layer includes a host and a dopant, the amount of the dopant may be in the range of about 0.01 parts by weight to about 15 parts by weight based on 100 parts by weight of the host, but embodiments of the present disclosure are not limited thereto.
The thickness of the emissive layer may be in the range of about
-about->
For example about->
-about->
Within a range of (2). When the thickness of the emission layer is within these ranges, excellent light emission characteristics can be obtained without a significant increase in driving voltage.
Next, the electron transport region is disposed on the emission layer.
The electron transport region may include a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.
For example, the electron transport region may have a hole blocking layer/electron transport layer/electron injection layer structure or an electron transport layer/electron injection layer structure, but the structure of the electron transport region is not limited thereto. The electron transport layer may have a multi-layer structure or a single-layer structure including two or more different materials.
The conditions for forming the hole blocking layer, the electron transporting layer, and the electron injecting layer constituting the electron transporting region may be similar to or the same as those for forming the hole injecting layer.
When the electron transport region includes a hole blocking layer, the hole blocking layer may include, for example, at least one of: 2, 9-dimethyl-4, 7-diphenyl-1, 10-phenanthroline (BCP), 4, 7-diphenyl-1, 10-phenanthroline (Bphen), or bis (2-methyl-8-hydroxyquinoline-N1, O8) - (1, 1' -biphenyl-4-hydroxy) aluminum (BAlq), although embodiments of the disclosure are not limited thereto:
the hole blocking layer may have a thickness of about
-about->
For example about->
-about->
Within a range of (2). When the thickness of the hole blocking layer is within these ranges, excellent hole blocking characteristics can be obtained without a significant increase in driving voltage.
The electron transport layer may include at least one of: BCP, bphen, tris (8-hydroxyquinoline) aluminum (Alq) 3 ) BAlq, 3- (4-biphenyl) -4-phenyl-5-tert-butylphenyl-1, 2, 4-Triazole (TAZ), or 4- (naphthalen-1-yl) -3, 5-diphenyl-4H-1, 2, 4-triazole (NTAZ):
in one or more embodiments, the electron transport layer may include at least one of the compounds ET1 to ET25, but embodiments of the present disclosure are not limited thereto:
the electron transport layer may have a thickness of about
-about->
For example about->
-about->
Within a range of (2). When the thickness of the electron transport layer is within these ranges, satisfactory electron transport characteristics can be obtained without a significant increase in driving voltage.
The electron transport layer may include a metal-containing material in addition to the materials described above.
The metal-containing material may include a Li complex. The Li complex may include, for example, the compound ET-D1 (lithium hydroxyquinoline (LiQ)) or ET-D2:
the electron transport region may include an electron injection layer that facilitates the flow of electrons from the second electrode 19 into it.
The electron injection layer may include LiF, naCl, csF, li 2 O, baO, or a combination thereof.
The electron injection layer may have a thickness of about
-about->
And e.g. about->
-about->
Within a range of (2). When the thickness of the electron injection layer is within these ranges, satisfactory electron injection characteristics can be obtained without a significant increase in driving voltage. />
A second electrode 19 is arranged on the organic layer 15. The second electrode 19 may be a cathode. The material used to form the second electrode 19 may be a metal, an alloy, a conductive compound, or a combination thereof having a relatively low work function. For example, a material for forming the second electrode 19 may be lithium (Li), magnesium (Mg), aluminum (Al), silver (Ag), aluminum-lithium (Al-Li), calcium (Ca), magnesium-indium (Mg-In), or magnesium-silver (Mg-Ag). In one or more embodiments, in order to manufacture a top emission type light emitting device, a transmissive electrode formed using ITO or IZO may be used as the second electrode 19.
Hereinabove, the organic light emitting device has been described with reference to fig. 1, but embodiments of the present disclosure are not limited thereto.
Another aspect of the present disclosure provides a diagnostic composition including at least one organometallic compound represented by formula 1.
The organometallic compound represented by formula 1 provides high luminous efficiency, and thus, the diagnostic composition including the at least one organometallic compound may have high diagnostic efficiency.
The diagnostic compositions are useful in a variety of applications including diagnostic kits, diagnostic reagents, biosensors, and biomarkers.
The term "C" as used herein 1 -C 60 Alkyl "refers to a straight or branched saturated aliphatic hydrocarbon monovalent radical having 1 to 60 carbon atoms andand examples thereof are methyl, ethyl, propyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, hexyl and the like. The term "C" as used herein 1 -C 60 Alkylene "means having a radical corresponding to C 1 -C 60 Divalent groups of the same structure as the alkyl group.
The term "C" as used herein 1 -C 60 Alkoxy "means a radical derived from-OA 101 (wherein A 101 Is C 1 -C 60 Alkyl), and examples thereof are methoxy, ethoxy, isopropoxy, and the like.
The term "C" as used herein 1 -C 60 Alkylthio "means a radical derived from-SA 101’ (wherein A 101’ Is C 1 -C 60 Alkyl) a monovalent group represented by an alkyl group.
The term "C" as used herein 2 -C 60 Alkenyl "means by at C 2 -C 60 The alkyl group is substituted with at least one carbon-carbon double bond at the middle or end thereof to form a hydrocarbon group, and examples thereof are vinyl, propenyl, butenyl, and the like. The term "C" as used herein 2 -C 60 Alkenylene "means having a radical corresponding to C 2 -C 60 Alkenyl groups are divalent radicals of the same structure.
The term "C" as used herein 2 -C 60 Alkynyl "means by at C 2 -C 60 The alkyl group is substituted with at least one carbon-carbon triple bond at the middle or end thereof to form a hydrocarbon group, and examples thereof are acetylene group, propynyl group, and the like. The term "C" as used herein 2 -C 60 Alkynylene "means having a radical different from C 2 -C 60 Alkynyl groups are divalent radicals of the same structure.
The term "C" as used herein 3 -C 10 Cycloalkyl "refers to a monovalent saturated hydrocarbon cyclic group having 3 to 10 carbon atoms, and examples thereof are cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and the like. The term "C" as used herein 3 -C 10 Cycloalkylene "means having a radical corresponding to C 3 -C 10 Cycloalkyl groups are divalent radicals of the same structure.
The term "C" as used herein 1 -C 10 Heterocycloalkyl "refers to a monovalent saturated cyclic group having at least one heteroatom selected from N, O, P, si, ge, se, and S as a ring-forming atom and 1 to 10 carbon atoms, and examples thereof are tetrahydrofuranyl, tetrahydrothienyl, and the like. The term "C" as used herein 1 -C 10 Heterocyclylene "means having a radical corresponding to C 1 -C 10 Divalent groups of the same structure as the heterocycloalkyl group.
The term "C" as used herein 3 -C 10 Cycloalkenyl "refers to a monovalent cyclic group having 3 to 10 carbon atoms and at least one carbon-carbon double bond in its ring and having no aromaticity, and examples thereof are cyclopentenyl, cyclohexenyl, cycloheptenyl, and the like. The term "C" as used herein 3 -C 10 Cycloalkenylene "means having a radical corresponding to C 3 -C 10 Divalent groups of the same structure as cycloalkenyl groups.
The term "C" as used herein 1 -C 10 Heterocycloalkenyl "refers to a monovalent cyclic group having at least one heteroatom selected from N, O, P, si, ge, se, and S in its ring as a ring-forming atom, 1-10 carbon atoms, and at least one double bond. C (C) 1 -C 10 Examples of heterocycloalkenyl are 2, 3-dihydrofuryl, 2, 3-dihydrothienyl, etc. The term "C" as used herein 1 -C 10 Heterocycloalkenylene "means having a structural formula corresponding to C 1 -C 10 Divalent groups of the same structure as the heterocycloalkenyl group.
The term "C" as used herein 6 -C 60 Aryl "refers to a monovalent group having a carbocyclic aromatic system of 6 to 60 carbon atoms, and the term" C "as used herein 6 -C 60 Arylene "refers to a divalent group having a carbocyclic aromatic system of 6 to 60 carbon atoms. C (C) 6 -C 60 Examples of aryl groups are phenyl, naphthyl, anthryl, phenanthryl, pyrenyl,
A base, etc. When C 6 -C 60 Aryl and C 6 -C 60 Where arylene groups each include two or more rings, the two or more rings may be fused to each other.
The term "C" as used herein 7 -C 60 Alkylaryl "means an alkylaryl group interrupted by at least one C 1 -C 54 Alkyl substituted C 6 -C 59 Aryl groups. The term "C" as used herein 7 -C 60 Arylalkyl "means an arylalkyl group which is substituted by at least one C 6 -C 59 Aryl substituted C 1 -C 54 An alkyl group.
The term "C" as used herein 1 -C 60 Heteroaryl "refers to a monovalent group having a cyclic aromatic system as follows: having at least one heteroatom selected from N, O, P, si, ge, se, and S as a ring forming atom, and 1 to 60 carbon atoms. The term "C" as used herein 1 -C 60 Heteroarylene "refers to a divalent group of a cyclic aromatic system as follows: having at least one heteroatom selected from N, O, P, ge, se, si, and S as a ring forming atom, and 1 to 60 carbon atoms. C (C) 1 -C 60 Examples of heteroaryl groups include pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, isoquinolinyl, and the like. When C 1 -C 60 Heteroaryl and C 1 -C 60 When each heteroaryl group includes two or more rings, the two or more rings may be fused to each other.
The term "C" as used herein 2 -C 60 Alkyl heteroaryl "means substituted with at least one C 1 -C 59 Alkyl substituted C 1 -C 59 Heteroaryl groups. The term "C" as used herein 2 -C 60 Heteroarylalkyl "means a radical containing at least one C 1 -C 59 Heteroaryl substituted C 1 -C 59 An alkyl group.
The term "C" as used herein 6 -C 60 Aryloxy "represents-OA 102 (wherein A 102 Is C 6 -C 60 Aryl), and the term "C" as used herein 6 -C 60 Arylthio "means-SA 103 (wherein A 103 Is C 6 -C 60 Aryl).
The term "C" as used herein 1 -C 60 Heteroaryloxy "means-OA 104 (wherein A 104 Is C 1 -C 60 Heteroaryl), and the term "C" as used herein 1 -C 60 Heteroarylthio "represents-SA 105 (wherein A 105 Is C 1 -C 60 Heteroaryl).
The term "monovalent non-aromatic fused polycyclic group" as used herein refers to a monovalent group (e.g., having 8 to 60 carbon atoms) as follows: it has two or more rings condensed with each other, has only carbon atoms as ring-forming atoms, and has no aromaticity in terms of its entire molecular structure. Examples of monovalent non-aromatic fused polycyclic groups are fluorenyl and the like. The term "divalent non-aromatic fused polycyclic group" as used herein refers to a divalent group having the same structure as the monovalent non-aromatic fused polycyclic groups described above.
The term "monovalent non-aromatic fused heteropolycyclic group" as used herein refers to a monovalent group (e.g., having 2 to 60 carbon atoms) as follows: it has two or more rings condensed with each other, has a heteroatom selected from N, O, P, si, ge, se, and S as a ring-forming atom in addition to a carbon atom, and has no aromaticity in terms of its entire molecular structure. Examples of monovalent non-aromatic fused heteropolycyclic groups are carbazolyl and the like. The term "divalent non-aromatic fused heteropolycyclic group" as used herein refers to a divalent group having the same structure as the monovalent non-aromatic fused heteropolycyclic groups described above.
The term "C" as used herein 5 -C 30 A carbocyclic group "refers to a saturated or unsaturated cyclic group having only 5 to 30 carbon atoms as ring-forming atoms. C (C) 5 -C 30 The carbocyclic group may be a monocyclic group or a polycyclic group.
The term "C" as used herein 1 -C 30 Heterocyclic group "means having at least one heteroatom selected from N, O, si, P, ge, se, and S in addition to 1 to 30 carbon atoms asSaturated or unsaturated cyclic groups which are ring-forming atoms. C (C) 1 -C 30 The heterocyclic group may be a monocyclic group or a polycyclic group.
In the present specification, TMS represents "-Si (CH) 3 ) 3 ", and TMG represents" -Ge (CH) 3 ) 3 ”。
Substituted C 5 -C 30 Carbocycle group, substituted C 1 -C 30 Heterocyclic groups, substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substituted C 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 1 -C 60 Alkylthio, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 1 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 7 -C 60 Alkylaryl, substituted C 7 -C 60 Arylalkyl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 Heteroaryl, substituted C 2 -C 60 Alkyl heteroaryl, substituted C 2 -C 60 Heteroarylalkyl, substituted C 1 -C 60 Heteroaryloxy, substituted C 1 -C 60 The at least one substituent of the heteroarylthio group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group may be:
deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H、-CDH 2 、-CF 3 、-CF 2 H、-CFH 2 Hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, or C 1 -C 60 Alkylthio;
c each substituted by at least one of 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, or C 1 -C 60 Alkylthio: deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H、-CDH 2 、-CF 3 、-CF 2 H、-CFH 2 Hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkylaryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si (Q) 11 )(Q 12 )(Q 13 )、-Ge(Q 11 )(Q 12 )(Q 13 )、-N(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 )、-P(Q 18 )(Q 19 )、-P(＝O)(Q 18 )(Q 19 ) Or a combination thereof;
C 3 -C 10 cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkylaryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, monovalent non-aromatic fused polycyclic group, or monovalent non-aromatic fused heteropolycyclic group;
each is as followsIs at least one substituted C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkylaryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, monovalent non-aromatic fused polycyclic groups, or monovalent non-aromatic fused heteropolycyclic groups: deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H、-CDH 2 、-CF 3 、-CF 2 H、-CFH 2 Hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 1 -C 60 Alkylthio, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkylaryl, C 7 -C 60 Arylalkyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 2 -C 60 Heteroarylalkyl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si (Q) 21 )(Q 22 )(Q 23 )、-Ge(Q 21 )(Q 22 )(Q 23 )、-N(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 )、-P(Q 28 )(Q 29 )、-P(＝O)(Q 28 )(Q 29 ) Or a combination thereof; or (b)
-Si(Q 31 )(Q 32 )(Q 33 )、-Ge(Q 31 )(Q 32 )(Q 33 )、-N(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 )、-P(Q 38 )(Q 39 ) or-P (=O) (Q 38 )(Q 39 ) A kind of electronic device
Q 1 -Q 9 、Q 11 -Q 19 、Q 21 -Q 29 And Q 31 -Q 39 Can be hydrogen, deuterium, -F, -Cl, -Br, -I, -SF, each independently 5 Hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 1 -C 60 Alkylthio, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 7 -C 60 Alkylaryl, substituted or unsubstituted C 7 -C 60 Arylalkyl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 Alkyl heteroaryl, substituted or unsubstituted C 2 -C 60 Heteroarylalkyl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 Heteroarylthio, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, or substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group.
Hereinafter, exemplary compounds and organic light emitting devices according to embodiments are described in further detail with reference to synthesis examples and examples. However, the compound and the organic light emitting device are not limited thereto. The phrase "using 'B' instead of 'a'" as used in describing the synthetic examples means that the amount of 'a' used is the same as the amount of 'B' used in terms of molar equivalents.
Examples
Synthesis example 1: synthesis of Compound 1
(1) Synthesis of Compound 1A (1)
2-phenylpyridine (5.2 g, 33.1 mmol) and iridium chloride trihydrate (IrCl) 3 (H 2 O) n N=3) (5.2 g,14.7 mmol) was mixed with 120 milliliters (mL) of ethoxyethanol and 40mL of Deionized (DI) water. The mixed solution was stirred and heated under reflux for 24 hours, then allowed to cool to room temperature. The resulting solid was isolated by filtration, washed thoroughly with water, methanol, and hexane in the stated order, and then dried in a vacuum oven to obtain 8.2g (92% yield) of compound 1A (1). Compound 1A (1) was then used in the next reaction without additional purification.
(2) Synthesis of Compound 1A
Compound 1A (1) (1.6 g,1.5 mmol) and 45mL of dichloromethane (MC) were mixed, and silver triflate (AgOTf) (0.8 g,3.1 mmol) was added to it after mixing with 15mL of methanol (MeOH). After that, the resultant reaction solution was stirred at room temperature for 18 hours while blocking light with aluminum foil, and the solid produced therein was removed by filtration through CELITE. The filtrate was depressurized to obtain a solid (compound 1A), which was then used in the next reaction without additional purification process.
(3) Synthesis of Compound 1B
2-chloro-4-isopropylpyridine (0.8 g,5.1 mmol) and 2, 3-diphenyl-9- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) -3H-benzo [2,3 ] under nitrogen]Benzofuro [6,7-d]Imidazole (2.8 g,5.7 mmol) was dissolved in 120mL of 1, 4-dioxane. Then, to the reaction mixture was added a solution containing potassium carbonate (K) 2 CO 3 ) (1.6 g,15.4 mmol) and to which was added a palladium catalyst (tetrakis (triphenylphosphine) palladium (0), pd (PPh) 3 ) 4 ) (0.30 g,0.26 mmol). Thereafter, the resulting reaction mixture was stirred and heated at 110℃under reflux. After allowing it to cool to room temperature, it is subjected to an extraction process, and the solid thus obtained is subjected to column chromatography (eluent: ethyl Acetate (EA) and hexane) to obtain 9- (4-isopropylpyridin-2-yl) -2, 3-diphenyl-3H-benzo [2,3 ] ]Benzofuro [6,7-d]Imidazole 2.2g (compound 1b,89% yield). The obtained compound was confirmed by high resolution mass spectrometry (HRMS (MALDI)) and High Performance Liquid Chromatography (HPLC) analysis using matrix-assisted laser desorption ionization.
HRMS (MALDI): for C 33 H 25 N 3 Calculated value of O: m/z:479.58, found: 479.92.
(4) Synthesis of Compound 1
Compound 1A (1.5 g,2.1 mmol) and compound 1B (2.3 g,1.9 mmol) were mixed with 20mL of 2-ethoxyethanol, then stirred and heated under reflux for 24 hours. Thereafter, the reaction temperature was lowered to room temperature. The resulting reaction mixture was decompressed, and the thus-obtained solid was subjected to column chromatography (eluent: dichloromethane (MC) and hexane) to obtain 0.7g (34% yield) of compound 1. The obtained compound was confirmed by HRMS (MALDI) and HPLC analysis.
HRMS (MALDI): for C 55 H 40 IrN 5 Calculated value of O: m/z:979.18, found: 979.78.
synthesis example 2: synthesis of Compound 2
Compound 2B was obtained in a similar manner as in the synthesis of compound 1B, except for the following: using 2-phenyl-9- (4, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) benzo [2,3 ]]Benzofuro [7,6-d]
Azole substituted 2, 3-diphenyl-9- (4, 5-tetramethyl-1, 3, 2-dioxapentaborane-2-yl) -3H-benzo [2,3 ] ]Benzofuro [6,7-d]Imidazole. Then, compound 2 was obtained in a similar manner to that in the synthesis of compound 1, except for the following: compound 2B was used instead of compound 1B. The obtained compound was confirmed by HRMS (MALDI) and HPLC analysis.
HRMS (MALDI): for C 49 H 35 IrN 4 O 2 Is calculated by the following steps: m/z:904.06, found: 904.99.
example 1
An ITO (as an anode) -patterned glass substrate was cut to a size of 50mm by 0.5mm, sonicated with isopropyl alcohol and DI water each for 5 minutes, and then cleaned by exposure to Ultraviolet (UV) rays and ozone for 30 minutes. The resulting ITO patterned glass substrate was loaded onto a vacuum deposition apparatus.
Vacuum co-depositing compound HT3 and compound F12 (p-dopant) on the anode at a weight ratio of 98:2 to form a cathode having
And vacuum depositing a compound HT3 on the hole injection layer to form a layer having +.>
A hole transport layer of a thickness of (a).
Then, compound GH3 (host) and compound 1 (dopant) were co-deposited on the hole transport layer in a weight ratio of 92:8 to form a polymer having
Is a layer of a thickness of the emissive layer.
Subsequently, the compounds ET3 and LiQ (n-dopant) were co-deposited on the emissive layer in a volume ratio of 50:50 to form a thin film having 
Vacuum depositing LiQ on the electron transport layer to form a thin film having a thickness of
And vacuum depositing Al on the electron injection layer to form an electron injection layer having +.>
And thus completing the fabrication of the organic light emitting device.
Example 2 and comparative examples 1 to 3
An organic light-emitting device was manufactured in a similar manner as in example 1, except that: in forming the emission layer, the compounds shown in table 2 were used as dopants instead of the compound 1, respectively.
The respective driving voltages (V), maximum external quantum efficiency (Max EQE,%), roll-off ratio (relative%), and maximum emission wavelength (λ) in the emission spectrum of the organic light emitting devices of examples 1 and 2 and comparative examples 1 to 3 were measured Maximum value Nm), and the results thereof are shown in table 2. As evaluation devices, a current-voltage meter (Keithley 2400) and a luminance meter (MinoltCs-1000A) were used. The roll-off ratio is calculated according to equation 20 and is shown in table 2.
Equation 20
Roll-off ratio= {1- (light-emitting efficiency/maximum light-emitting efficiency) } ×100%
TABLE 2
From table 2, it was confirmed that the organic light emitting devices of examples 1 and 2 have excellent EQE, and low driving voltage and roll-off ratio. It was also confirmed that the organic light emitting devices of examples 1 and 2 had lower driving voltages, lower roll-off ratios, and higher or comparable EQEs relative to the organic light emitting devices of comparative examples 1 to 3.
As described above, according to one or more embodiments, the organometallic compound may have excellent electrical characteristics and thermal stability. In particular, the organometallic compound has a high glass transition temperature, so that crystallization thereof can be prevented and electric mobility thereof can be improved. Thus, an electronic device, such as an organic light emitting device, using the organometallic compound may have a low driving voltage, high efficiency, long lifetime, reduced roll-off ratio, and relatively narrow FWHM of an emission peak in an electroluminescence spectrum.
Therefore, a high quality organic light emitting device can be realized due to the use of the organometallic compound. Further, an electronic apparatus including the organic light emitting device may be provided.
It should be understood that the exemplary embodiments described herein should be considered in descriptive sense only and not for purposes of limitation. The descriptions of features or aspects in various exemplary embodiments should typically be considered as available for other similar features or aspects of other exemplary embodiments. Although one or more exemplary embodiments have been described with reference to the accompanying drawings, it will be understood by those of ordinary skill in the art that various changes in form and details may be made therein without departing from the spirit and scope as defined by the following claims.
Claims (20)
1. An organometallic compound represented by formula 1:
1 (1)
M 1 (Ln 1 ) n1 (Ln 2 ) n2
Wherein, in the formula 1,
M 1 in the case of a transition metal, the transition metal,
Ln 1 is a ligand represented by the formula 1A,
Ln 2 is a ligand represented by the formula 1B,
n1 is 1 or 2, and
n2 is 1 or 2 and is preferably selected from the group consisting of,
wherein, in the formulas 1A and 1B,
ring CY 1 And a ring CY 2 Each independently is C 5 -C 30 Carbocyclic group or C 1 -C 30 A heterocyclic group which is a heterocyclic group,
ring CY 41 Is a group of benzene, and is a group of benzene,
ring CY 42 Is a 5-membered aromatic heterocyclic group,
X 1 is C or N, and X 2 Is C or N, and is not limited to the above,
Y 1 o, S, se, C (R) 3 )(R 4 )、N(R 3 ) Or B (R) 3 )，
R 1 -R 4 、R 10 、R 20 、R 31 -R 34 And R is 40 Each independently is hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 Hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, substituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 1 -C 60 Alkylthio, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 7 -C 60 Alkylaryl, substituted or unsubstituted C 7 -C 60 Arylalkyl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 Alkyl heteroaryl, substituted or unsubstituted C 2 -C 60 Heteroarylalkyl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 Heteroarylthio, substituted or unsubstituted monovalent non-aromatic fused polycyclic group, substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, -Si (Q) 1 )(Q 2 )(Q 3 )、-Ge(Q 1 )(Q 2 )(Q 3 )、-N(Q 4 )(Q 5 )、-B(Q 6 )(Q 7 )、-P(Q 8 )(Q 9 ) or-P (=O) (Q 8 )(Q 9 )，
Multiple R' s 10 Optionally linked together to form a substituted or unsubstituted C 5 -C 30 Carbocyclic groups or substituted or unsubstituted C 1 -C 30 A heterocyclic group which is a heterocyclic group,
multiple R' s 20 Optionally linked together to form a substituted or unsubstituted C 5 -C 30 Carbocyclic groups or substituted or unsubstituted C 1 -C 30 A heterocyclic group which is a heterocyclic group,
R 1 -R 4 、R 10 、R 20 、R 31 -R 34 and R is 40 Optionally linked together to form a substituted or unsubstituted C 5 -C 30 Carbocyclic groups or substituted or unsubstituted C 1 -C 30 A heterocyclic group which is a heterocyclic group,
b10 and b20 are each independently 1, 2, 3, 4, 5, 6, 7, 8, 9 or 10,
b40 is 0, 1, 2, 3, 4 or 5,
substituted C 5 -C 30 Carbocycle group, substituted C 1 -C 30 Heterocyclic groups, substituted C 1 -C 60 Alkyl, substituted C 2 -C 60 Alkenyl, substitutedC 2 -C 60 Alkynyl, substituted C 1 -C 60 Alkoxy, substituted C 1 -C 60 Alkylthio, substituted C 3 -C 10 Cycloalkyl, substituted C 1 -C 10 Heterocycloalkyl, substituted C 3 -C 10 Cycloalkenyl, substituted C 1 -C 10 Heterocycloalkenyl, substituted C 6 -C 60 Aryl, substituted C 7 -C 60 Alkylaryl, substituted C 7 -C 60 Arylalkyl, substituted C 6 -C 60 Aryloxy, substituted C 6 -C 60 Arylthio, substituted C 1 -C 60 Heteroaryl, substituted C 2 -C 60 Alkyl heteroaryl, substituted C 2 -C 60 Heteroarylalkyl, substituted C 1 -C 60 Heteroaryloxy, substituted C 1 -C 60 At least one substituent of the heteroarylthio group, the substituted monovalent non-aromatic fused polycyclic group, and the substituted monovalent non-aromatic fused heteropolycyclic group is:
deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H、-CDH 2 、-CF 3 、-CF 2 H、-CFH 2 Hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy or C 1 -C 60 Alkylthio;
c each substituted by at least one of 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy or C 1 -C 60 Alkylthio: deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H、-CDH 2 、-CF 3 、-CF 2 H、-CFH 2 Hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkylaryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si (Q) 11 )(Q 12 )(Q 13 )、-Ge(Q 11 )(Q 12 )(Q 13 )、-N(Q 14 )(Q 15 )、-B(Q 16 )(Q 17 )、-P(Q 18 )(Q 19 )、-P(＝O)(Q 18 )(Q 19 ) Or a combination thereof;
C 3 -C 10 cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkylaryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, monovalent non-aromatic fused polycyclic groups or monovalent non-aromatic fused heteropolycyclic groups;
c each substituted by at least one of 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkylaryl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, monovalent non-aromatic fused polycyclic group or monovalent non-aromatic fused heteropolycyclic group: deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H、-CDH 2 、-CF 3 、-CF 2 H、-CFH 2 Hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy, C 1 -C 60 Alkylthio, C 3 -C 10 Cycloalkyl, C 1 -C 10 Heterocycloalkyl, C 3 -C 10 Cycloalkenyl, C 1 -C 10 Heterocycloalkenyl, C 6 -C 60 Aryl, C 7 -C 60 Alkylaryl, C 7 -C 60 Arylalkyl, C 6 -C 60 Aryloxy, C 6 -C 60 Arylthio, C 1 -C 60 Heteroaryl, C 2 -C 60 Alkyl heteroaryl, C 2 -C 60 Heteroarylalkyl, C 1 -C 60 Heteroaryloxy, C 1 -C 60 Heteroarylthio, monovalent non-aromatic fused polycyclic group, monovalent non-aromatic fused heteropolycyclic group, -Si (Q) 21 )(Q 22 )(Q 23 )、-Ge(Q 21 )(Q 22 )(Q 23 )、-N(Q 24 )(Q 25 )、-B(Q 26 )(Q 27 )、-P(Q 28 )(Q 29 )、-P(＝O)(Q 28 )(Q 29 ) Or a combination thereof; or (b)
-Si(Q 31 )(Q 32 )(Q 33 )、-Ge(Q 31 )(Q 32 )(Q 33 )、-N(Q 34 )(Q 35 )、-B(Q 36 )(Q 37 )、-P(Q 38 )(Q 39 ) or-P (=O) (Q 38 )(Q 39 )，
Q 1 -Q 9 、Q 11 -Q 19 、Q 21 -Q 29 And Q 31 -Q 39 Each independently is hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 Hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, and the likeSubstituted or unsubstituted C 1 -C 60 Alkyl, substituted or unsubstituted C 2 -C 60 Alkenyl, substituted or unsubstituted C 2 -C 60 Alkynyl, substituted or unsubstituted C 1 -C 60 Alkoxy, substituted or unsubstituted C 1 -C 60 Alkylthio, substituted or unsubstituted C 3 -C 10 Cycloalkyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkyl, substituted or unsubstituted C 3 -C 10 Cycloalkenyl, substituted or unsubstituted C 1 -C 10 Heterocycloalkenyl, substituted or unsubstituted C 6 -C 60 Aryl, substituted or unsubstituted C 7 -C 60 Alkylaryl, substituted or unsubstituted C 7 -C 60 Arylalkyl, substituted or unsubstituted C 6 -C 60 Aryloxy, substituted or unsubstituted C 6 -C 60 Arylthio, substituted or unsubstituted C 1 -C 60 Heteroaryl, substituted or unsubstituted C 2 -C 60 Alkyl heteroaryl, substituted or unsubstituted C 2 -C 60 Heteroarylalkyl, substituted or unsubstituted C 1 -C 60 Heteroaryloxy, substituted or unsubstituted C 1 -C 60 Heteroarylthio, substituted or unsubstituted monovalent non-aromatic fused polycyclic group or substituted or unsubstituted monovalent non-aromatic fused heteropolycyclic group, and
* And' each represents a group corresponding to M 1 Is a binding site for a polypeptide.
2. The organometallic compound according to claim 1, wherein M 1 Is iridium (Ir), platinum (Pt), osmium (Os), titanium (Ti), zirconium (Zr), hafnium (Hf), europium (Eu), terbium (Tb), thulium (Tm) or rhodium (Rh).
3. The organometallic compound according to claim 1, wherein
M 1 Is Ir, and
the sum of n1 and n2 is 3.
4. The organometallic compound according to claim 1, wherein the cyclic CY 1 And a ring CY 2 Each independently is a phenyl group, a naphthalene group, a 1,2,3, 4-tetrahydronaphthalene group, a phenanthrene group, a pyridine group, a pyrimidine group, a pyrazine group, a pyridazine group, a triazine group, a quinoline group, an isoquinoline group, a quinoxaline group, a quinazoline group, a phenanthroline group, a benzofuran group, a benzothiophene group, a fluorene group, a carbazole group, a dibenzofuran group, a dibenzothiophene group, a dibenzosilole group, an azafluorene group, an azacarbazole group, an azadibenzofuran group, an azadibenzothiophene group, or an azadibenzosilole group.
5. The organometallic compound according to claim 1, wherein the cyclic CY 42 Is furan group, thiophene group, selenophene group, pyrrole group, boro-heterocyclo pentadiene group,
An azole group, a thiazole group, a selenazole group, an imidazole group, an azaborole group, an oxaborole group, a thiaborole group, a selenoboropentadiene group, or a diboron pentadiene group.
6. The organometallic compound according to claim 1, wherein the cyclic CY 1 Represented by one of formulas 1-1 to 1-16:
wherein, in the formulas 1-1 to 1-16,
R 11 -R 14 each independently as in claim 1 for R 10 Defined under the condition that R 11 -R 14 Each other than hydrogen, and
* Representation and M 1 And represents a binding site to an adjacent atom.
7. The organogold of claim 1Genus compound in which the ring CY 2 Represented by one of formulas 2-1 to 2-16:
wherein, in the formulas 2-1 to 2-16,
R 21 -R 24 each independently as in claim 1 for R 20 Defined under the condition that R 21 -R 24 Each other than hydrogen, and
* Representation and M 1 And "indicates the binding site to an adjacent atom.
8. The organometallic compound according to claim 1, wherein R 1 -R 4 、R 10 、R 20 、R 31 -R 34 And R is 40 Each independently is:
Hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H、-CDH 2 、-CF 3 、-CF 2 H、-CFH 2 Hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy or C 1 -C 20 Alkylthio;
c each substituted by at least one of 1 -C 20 Alkyl, C 1 -C 20 Alkoxy or C 1 -C 20 Alkylthio: deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H、-CDH 2 、-CF 3 、-CF 2 H、-CFH 2 Hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C 1 -C 10 Alkyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthaleneA group, a pyridinyl group, a pyrimidinyl group, or a combination thereof;
cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo [9,10 ]]Phenanthryl, pyrenyl, and,
A group, a pyrrolyl group, a thienyl group, a furyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, and a +.>
Azolyl, iso->
Oxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, isobenzothiazolyl, benzo- >
Azolyl, isobenzo->
Oxazolyl, triazolyl, tetrazolyl, < >>
Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl or imidazopyrimidinyl;
cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norbornenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl,Anthracenyl, fluoranthenyl, benzo [9,10]Phenanthryl, pyrenyl, and,
A group, a pyrrolyl group, a thienyl group, a furyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, and a +.>
Azolyl, iso->
Oxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, isobenzothiazolyl, benzo->
Azolyl, isobenzo->
Oxazolyl, triazolyl, tetrazolyl, < >>
Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl or imidazopyrimidinyl: deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H、-CDH 2 、-CF 3 、-CF 2 H、-CFH 2 Hydroxyl, cyano, nitro, amino, amidino, hydrazino, hydrazone, carboxylic acid or salt thereof, sulfonic acid or salt thereof, phosphoric acid or salt thereof, C 1 -C 20 Alkyl, C 1 -C 20 Alkoxy, C 1 -C 20 Alkylthio, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, adamantyl, norbornyl, norborneneAlkenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, phenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, benzo [9,10 ]]Phenanthryl, pyrenyl,>
a group, a pyrrolyl group, a thienyl group, a furyl group, an imidazolyl group, a pyrazolyl group, a thiazolyl group, an isothiazolyl group, and a +.>
Azolyl, iso->
Oxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, isoindolyl, indolyl, indazolyl, purinyl, quinolinyl, isoquinolinyl, benzoquinolinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, phenanthrolinyl, benzimidazolyl, benzofuranyl, benzothienyl, isobenzothiazolyl, benzo->
Azolyl, isobenzo->
Oxazolyl, triazolyl, tetrazolyl, < >>
Diazolyl, triazinyl, dibenzofuranyl, dibenzothiophenyl, benzocarbazolyl, dibenzocarbazolyl, imidazopyridinyl, imidazopyrimidinyl, or a combination thereof; or (b)
-Si(Q 1 )(Q 2 )(Q 3 )、-Ge(Q 1 )(Q 2 )(Q 3 )、-N(Q 4 )(Q 5 )、-B(Q 6 )(Q 7 )、-P(Q 8 )(Q 9 ) or-P (=O) (Q 8 )(Q 9 ) A kind of electronic device
Q 1 -Q 9 Each independently is:
-CH 3 、-CD 3 、-CD 2 H、-CDH 2 、-CH 2 CH 3 、-CH 2 CD 3 、-CH 2 CD 2 H、-CH 2 CDH 2 、-CHDCH 3 、-CHDCD 2 H、-CHDCDH 2 、-CHDCD 3 、-CD 2 CD 3 、-CD 2 CD 2 h or-CD 2 CDH 2 ；
N-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl or naphthyl; or (b)
N-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, sec-pentyl, tert-pentyl, phenyl or naphthyl each being substituted with at least one of: deuterium, C 1 -C 10 Alkyl, phenyl, or a combination thereof.
9. The organometallic compound according to claim 1, wherein R 1 -R 4 、R 10 、R 20 、R 31 -R 34 And R is 40 Each independently is:
hydrogen, deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H、-CDH 2 、-CF 3 、-CF 2 H、-CFH 2 、C 1 -C 60 Alkyl, C 2 -C 60 Alkenyl, C 2 -C 60 Alkynyl, C 1 -C 60 Alkoxy or C 1 -C 60 Alkylthio;
a group represented by one of formulas 9-1 to 9-61, 9-201 to 9-237, 10-1 to 10-129, and 10-201 to 10-350; or (b)
-Si(Q 1 )(Q 2 )(Q 3 )、-Ge(Q 1 )(Q 2 )(Q 3 ) or-N (Q) 4 )(Q 5 )：
Wherein, in formulas 9-1 to 9-61, 9-201 to 9-237, 10-1 to 10-129, and 10-201 to 10-350, representing binding sites to adjacent atoms, "Ph" is phenyl, "TMS" is trimethylsilyl, and "TMG" is trimethylgermyl.
10. The organometallic compound according to claim 1, wherein R 10 、R 20 And R is 31 -R 34 At least one of (C) is deuterium, -F, -Cl, -Br, -I, -SF 5 、-CD 3 、-CD 2 H、-CDH 2 、-CF 3 、-CF 2 H、-CFH 2 、C 1 -C 60 Alkyl or C substituted by at least one deuterium 1 -C 60 An alkyl group.
11. As claimed inThe organometallic compound according to 1, wherein Ln 2 Represented by one of formulas 11-1 to 11-3:
wherein, in the formulas 11-1 to 11-3,
R 1 、R 2 、R 31 -R 34 、R 40 、CY 42 and Y 1 As defined in claim 1 respectively,
b41 is 1, 2 or 3,
R 41 and R is 44 Each independently as in claim 1 for R 40 Defined, and
* And' each represents a group corresponding to M 1 Is a binding site for a polypeptide.
12. The organometallic compound according to claim 1, wherein Ln 2 Represented by one of formulas 21-1 to 21-6:
wherein, in the formulas 21-1 to 21-6,
R 1 、R 2 、R 31 -R 34 and Y 1 As defined in claim 1,
X 41 n, B or C (R) 46 )，
X 42 O, S, se, N (R) 47 ) Or B (R) 47 )，
R 41 -R 47 Each independently as in claim 1 for R 40 Defined, and
* And' each represents a group corresponding to M 1 Is a binding site for a polypeptide.
13. The organometallic compound according to claim 1, wherein the organometallic compound is a compound represented by one of formulas 31-1 to 31-6:
wherein, in the formulas 31-1 to 31-6,
M 1 、n1、n2、Y 1 、R 1 and R is 2 As defined in claim 1,
X 11 is C (R) 11 ) Or N, X 12 Is C (R) 12 ) Or N, X 13 Is C (R) 13 ) Or N, and X 14 Is C (R) 14 ) Or N, or a combination of two,
X 21 is C (R) 21 ) Or N, X 22 Is C (R) 22 ) Or N, X 23 Is C (R) 23 ) Or N, and X 24 Is C (R) 24 ) Or N, or a combination of two,
X 41 n, B or C (R) 46 )，
X 42 O, S, se, N (R) 47 ) Or B (R) 47 )，
R 11 -R 14 Each independently as in claim 1 for R 10 As defined in the definition of the term "a" or "b",
R 21 -R 24 each independently as in claim 1 for R 20 As defined in the definition of the term "a" or "b",
R 31 -R 34 each independently as defined in claim 1,
R 43 -R 47 each independently as in claim 1 for R 40 As defined in the definition of the term "a" or "b",
R 11 -R 14 optionally linked to each other to form a group which is unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 A heterocyclic group which is a heterocyclic group,
R 21 -R 24 optionally linked to each other to form a group which is unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 A heterocyclic group which is a heterocyclic group,
R 31 -R 34 optionally linked to each other to form a group which is unsubstituted or substituted with at least one R 10a Substituted C 5 -C 30 Carbocyclic groups are either unsubstituted or substituted with at least one R 10a Substituted C 1 -C 30 A heterocyclic group, and
R 10a r as in claim 1 10 As defined.
14. The organometallic compound of claim 1, wherein the organometallic compound is one of compounds 1 to 73:
15. an organic light emitting device, comprising:
a first electrode;
a second electrode; and
an organic layer disposed between the first electrode and the second electrode,
Wherein the organic layer comprises an emissive layer, and
wherein the organic layer comprises at least one organometallic compound according to any of claims 1-14.
16. The organic light emitting device of claim 15, wherein the emissive layer comprises the at least one organometallic compound.
17. The organic light-emitting device of claim 16,
wherein the emissive layer further comprises a host, and
wherein the amount of the host in the emissive layer is greater than the amount of the at least one organometallic compound in the emissive layer.
18. The organic light-emitting device of claim 16, wherein the emissive layer emits blue light having a maximum emission wavelength in the range of 500 nm-600 nm.
19. The organic light-emitting device of claim 16, wherein
The first electrode is an anode and the second electrode is an anode,
the second electrode is a cathode electrode and,
the organic layer further includes a hole transport region disposed between the first electrode and the emission layer and an electron transport region disposed between the emission layer and the second electrode,
the hole transport region comprises a hole injection layer, a hole transport layer, an electron blocking layer, a buffer layer, or a combination thereof, and
The electron transport region includes a hole blocking layer, an electron transport layer, an electron injection layer, or a combination thereof.
20. An electronic device comprising an organic light emitting device according to any one of claims 15-19.
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| KR1020220132734A KR20230057271A (en) | 2021-10-21 | 2022-10-14 | Organometallic compound, organic light emitting device including the same and electronic apparatus comprising organic light emitting device |
| KR10-2022-0132734 | 2022-10-14 |
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